Organometallic compound and organic light-emitting device including the same

ABSTRACT

An organometallic compound represented by Formula 1: 
     
       
         
         
             
             
         
       
         
         
           
             wherein, in Formula 1, groups and variables are the same as described in the specification.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to Korean Patent Application Nos.10-2015-0116207, filed on Aug. 18, 2015, and 10-2016-0101888, filed onAug. 10, 2016, in the Korean Intellectual Property Office, and all thebenefits accruing therefrom under 35 U.S.C. §119, the contents of whichare incorporated herein in their entirety by reference.

BACKGROUND

1. Field

Embodiments relate to an organometallic compound and an organiclight-emitting device including the same.

2. Description of the Related Art

Organic light-emitting devices (OLEDs) are self-emission devices thathave wide viewing angles, high contrast ratios, and short responsetimes. In addition, the OLEDs display excellent brightness, drivingvoltage, and response speed characteristics, and produce full-colorimages.

In an example, an organic light-emitting device includes an anode, acathode, and an organic layer disposed between the anode and thecathode, wherein the organic layer includes an emission layer. A holetransport region may be disposed between the anode and the emissionlayer, and an electron transport region may be disposed between theemission layer and the cathode. Holes provided from the anode may movetoward the emission layer through the hole transport region, andelectrons provided from the cathode may move toward the emission layerthrough the electron transport region. The holes and the electronsrecombine in the emission layer to produce excitons. These excitonstransition from an excited state to a ground state, thereby generatinglight.

Various types of organic light emitting devices are known. However,there still remains a need in OLEDs having low driving voltage, highefficiency, high brightness, and long lifespan.

SUMMARY

Provided are an organometallic compound and an organic light-emittingdevice including the same.

Additional aspects will be set forth in part in the description whichfollows and, in part, will be apparent from the description, or may belearned by practice of the presented embodiments.

According to an aspect of an embodiment, an organometallic compound isrepresented by Formula 1:

In Formula 1,

M may be selected from a Period 1 transition metal, a Period 2transition metal, and a Period 3 transition metal;

A₁ to A₄ may each independently be selected from a C₅-C₂₀ carbocyclicgroup and a C₁-C₂₀ heterocyclic group;

X₁ to X₄ may each independently be selected from a carbon atom (C) and anitrogen atom (N), provided that at least one selected from X₃ and X₄may be N;

B₁ to B₄ may each independently be selected from a single bond, O, andS;

Y₁ to Y₃ may each independently be selected from a single bond and adivalent linking group, and at least one of Y₁ to Y₃ is a divalentlinking group;

Z₁ and Z₂ may each independently be represented by one of Formulae 2-1to 2-4:

wherein, in Formulae 2-1 to 2-4,

Y₂₁ and Y₂₂ may each independently be selected from a substituted orunsubstituted C₁-C₁₀ alkylene group and a substituted or unsubstitutedC₂-C₁₀ alkenylene group;

a21 and a22 may each independently be selected from 0, 1, 2, 3, 4, and5;

R₂₁ to R₂₇ may each independently be selected from hydrogen, deuterium,a substituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₇-C₆₀ arylalkyl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group;

d1 and d2 may each independently be selected from 0, 1, 2, 3, and 4;

when d1 is 2 or more, groups Z₁ may be identical to or different fromeach other, when d2 is 2 or more, groups Z₂ may be identical to ordifferent from each other;

when X₃ is N, d1 may be selected from 1, 2, 3, and 4; or when X₄ is N,d2 may be selected from 1, 2, 3, and 4;

R₁ to R₄ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₇-C₆₀ arylalkyl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryl group, a substituted or unsubstituted C₁-C₆₀heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group, —C(═O)(Q₇),and —N(Q₇)(Q₈); R₁ and R₄ or R₂ and R₃ may optionally be linked to eachother to form a saturated or unsaturated ring;

Q₇ and Q₈ may each independently be selected from a C₁-C₆₀ alkyl groupand a C₆-C₆₀ aryl group;

b1 to b4 may each independently selected from 1, 2, 3, and 4;

L₁ may be selected from a monodentate ligand and a bidentate ligand;

a1 may be selected from 0, 1, and 2; and

* indicates a binding site to a neighboring atom.

Another aspect provides an organic light-emitting device including:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the secondelectrode,

wherein the organic layer includes an emission layer and at least oneorganometallic compound represented by Formula 1.

BRIEF DESCRIPTION OF THE DRAWING

These and/or other aspects will become apparent and more readilyappreciated from the following description of the embodiments, taken inconjunction with FIG. 1 which is a schematic cross-sectional view of anorganic light-emitting device according to an embodiment.

DETAILED DESCRIPTION

Reference will now be made in detail to embodiments, examples of whichare illustrated in the accompanying drawings, wherein like referencenumerals refer to like elements throughout. In this regard, the presentembodiments may have different forms and should not be construed asbeing limited to the descriptions set forth herein. Accordingly, theembodiments are merely described below, by referring to the FIGS., toexplain aspects. As used herein, the term “and/or” includes any and allcombinations of one or more of the associated listed items. Expressionssuch as “at least one of,” when preceding a list of elements, modify theentire list of elements and do not modify the individual elements of thelist.

The present disclosure will now be described more fully with referenceto exemplary embodiments. The disclosure may, however, be embodied inmany different forms and should not be construed as being limited to theembodiments set forth herein; rather, these embodiments are provided sothat this disclosure will be thorough and complete, and will fullyconvey the concept of the disclosure to those skilled in the art.Advantages, features, and how to achieve them of the present inventiveconcept will become apparent by reference to the embodiment that will bedescribed later in detail, together with the accompanying drawings. Thisinventive concept may, however, be embodied in many different forms andshould not be limited to the exemplary embodiments.

Hereinafter, embodiments are described in detail by referring to theattached drawings, and in the drawings, like reference numerals denotelike elements, and a redundant explanation thereof will not be providedherein.

It will be understood that, although the terms first, second, third etc.may be used herein to describe various elements, components, regions,layers, and/or sections, these elements, components, regions, layers,and/or sections should not be limited by these terms. These terms areonly used to distinguish one element, component, region, layer, orsection from another element, component, region, layer, or section.Thus, a first element, component, region, layer, or section discussedbelow could be termed a second element, component, region, layer, orsection without departing from the teachings of the present embodiments.

As used herein, the singular forms “a,” “an” and “the” are intended toinclude the plural forms as well, unless the context clearly indicatesotherwise.

The term “or” means “and/or.” It will be further understood that theterms “comprises” and/or “comprising” or “includes” and/or “including”used herein specify the presence of stated features, regions, integers,steps, operations, elements, and/or components, but do not preclude thepresence or addition of one or more other features, regions, integers,steps, operations, elements, and/or components.

It will be understood that when a layer, region, or component isreferred to as being “on” or “onto” another layer, region, or component,it may be directly or indirectly formed on the other layer, region, orcomponent. That is, for example, intervening layers, regions, orcomponents may be present.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which this general inventive conceptbelongs. It will be further understood that terms, such as those definedin commonly used dictionaries, should be interpreted as having a meaningthat is consistent with their meaning in the context of the relevant artand the present disclosure, and will not be interpreted in an idealizedor overly formal sense unless expressly so defined herein.

Exemplary embodiments are described herein with reference to crosssection illustrations that are schematic illustrations of idealizedembodiments. As such, variations from the shapes of the illustrations asa result, for example, of manufacturing techniques and/or tolerances,are to be expected. Thus, embodiments described herein should not beconstrued as limited to the particular shapes of regions as illustratedherein but are to include deviations in shapes that result, for example,from manufacturing. For example, a region illustrated or described asflat may, typically, have rough and/or nonlinear features. Moreover,sharp angles that are illustrated may be rounded. Thus, the regionsillustrated in the FIGS. are schematic in nature and their shapes arenot intended to illustrate the precise shape of a region and are notintended to limit the scope of the present claims.

Sizes of components in the drawings may be exaggerated for convenienceof explanation. In other words, since sizes and thicknesses ofcomponents in the drawings are arbitrarily illustrated for convenienceof explanation, the following embodiments are not limited thereto.

“About” or “approximately” as used herein is inclusive of the statedvalue and means within an acceptable range of deviation for theparticular value as determined by one of ordinary skill in the art,considering the measurement in question and the error associated withmeasurement of the particular quantity (i.e., the limitations of themeasurement system). For example, “about” can mean within one or morestandard deviations, or within ±30%, 20%, 10%, 5% of the stated value.

The term “organic layer” as used herein refers to a single layer and/ora plurality of layers between the first electrode and the secondelectrode of the organic light-emitting device. A material included inthe “organic layer” is not limited to an organic material.

An organometallic compound according to an embodiment is represented byFormula 1:

In Formula 1, M may be selected from a Period 1 transition metal, aPeriod 2 transition metal, and a Period 3 transition metal.

For example, M in Formula 1 may be selected from iridium (Ir), platinum(Pt), osmium (Os), ruthenium (Ru), rhodium (Rh), palladium (Pd), copper(Cu), silver (Ag), gold (Au), titanium (Ti), zirconium (Zr), hafnium(Hf), europium (Eu), terbium (Tb), and thulium (Tm), but is not limitedthereto.

In an embodiment, M in Formula 1 may be selected from Ir, Pt, Os, Ti,Zr, Hf, Eu, Tb, and Tm, but is not limited thereto.

In an embodiment, M in Formula 1 may be selected from Ir, Pt, and Os,but is not limited thereto.

In an embodiment, M in Formula 1 may be Pt, but is not limited thereto.

A₁ to A₄ in Formula 1 may each independently be selected from a C₅-C₂₀carbocyclic group and a C₁-C₂₀ heterocyclic group.

For example, A₁ to A₄ in Formula 1 may each independently be selectedfrom a C₅-C₂₀ carbocyclic group and a C₁-C₂₀ heterocyclic group; and

at least one selected from A₃ and A₄ may be a C₁-C₂₀ heterocyclic group,but they are not limited thereto.

In an embodiment, A₁ to A₄ in Formula 1 may each independently beselected from a benzene group, a naphthalene group, a pyrrole group, animidazole group, a pyrazole group, a thiazole group, an isothiazolegroup, an oxazole group, an isoxazole group, a triazole group, anindazole group, a tetrahydroindazole group, a pyridine group, a thiazinegroup, an oxazine group, a pyrimidine group, a pyrazine group, apyridazine group, a triazine group, a quinoline group, an isoquinolinegroup, a quinoxaline group, a quinazoline group, naphthyridine group, anindole group, a benzimidazole group, a benzothiazole group, abenzoisothiazole group, a benzoxazole group, a benzoiso-oxazole group, abenzothiazine group, a benzoxazine group, a dibenzofuran group, and adibenzothiophene group; and

at least one selected from A₃ and A₄ may be selected from a pyrrolegroup, an imidazole group, a pyrazole group, a thiazole group, anisothiazole group, an oxazole group, an isoxazole group, a triazolegroup, an indazole group, a tetrahydroindazole group, a pyridine group,a thiazine group, an oxazine group, a pyrimidine group, a pyrazinegroup, a pyridazine group, a triazine group, a quinoline group, anisoquinoline group, a quinoxaline group, a quinazoline group,naphthyridine group, an indole group, a benzimidazole group, abenzothiazole group, a benzoisothiazole group, a benzoxazole group, abenzoiso-oxazole group, a benzothiazine group, and a benzoxazine group,but they are not limited thereto.

In an embodiment, A₁ to A₄ in Formula 1 may each independently beselected from a benzene group, a naphthalene group, a pyrazole group, anindazole group, a tetrahydroindazole group, a pyridine group, apyrimidine group, a pyrazine group, a pyridazine group, a quinolinegroup, an isoquinoline group, an indole group, a benzimidazole group, adibenzofuran group, and a dibenzothiophene group; and

at least one selected from A₃ and A₄ may be selected from a pyrazolegroup, an indazole group, a tetrahydroindazole group, a pyridine group,a pyrimidine group, a pyrazine group, a pyridazine group, a quinolinegroup, an isoquinoline group, an indole group, and a benzimidazolegroup, but they are not limited thereto.

In an embodiment, A₁ to A₄ in Formula 1 may each independently beselected from a benzene group, a naphthalene group, a pyrazole group, anindazole group, a tetrahydroindazole group, a pyridine group, apyrimidine group, a pyrazine group, a pyridazine group, a quinolinegroup, an isoquinoline group, an indole group, a benzimidazole group, adibenzofuran group, and a dibenzothiophene group; and

at least one selected from A₃ and A₄ may be selected from a pyrazolegroup, an indazole group, a tetrahydroindazole group, a pyridine group,a pyrimidine group, a pyrazine group, a pyridazine group, a quinolinegroup, an isoquinoline group, an indole group, and a benzimidazolegroup, but they are not limited thereto.

In an embodiment, A₁ to A₄ in Formula 1 may each independently beselected from a benzene group, a naphthalene group, a pyridine group, apyrimidine group, a pyrazine group, a quinoline group, an isoquinolinegroup, a dibenzofuran group, and a dibenzothiophene group; and

at least one selected from A₃ and A₄ may be selected from a pyridinegroup, a pyrimidine group, a pyrazine group, a quinoline group, and anisoquinoline group, but they are not limited thereto.

In an embodiment, A₁ to A₄ in Formula 1 may each independently beselected from a benzene group, a naphthalene group, a pyridine group, apyrimidine group, a quinoline group, an isoquinoline group, and adibenzofuran group; and

at least one selected from A₃ and A₄ may be selected from a pyridinegroup, a pyrimidine group, a quinoline group, and an isoquinoline group,but they are not limited thereto.

X₁ to X₄ in Formula 1 may each independently be selected from a carbonatom (C) and a nitrogen atom (N), provided that at least one selectedfrom X₃ and X₄ may be N.

For example, X₁ and X₂ in Formula 1 may be C;

X₃ and X₄ may each independently be selected from C and N, and at leastone selected from X₃ and X₄ may be N, but they are not limited thereto.

In an embodiment, X₁ and X₂ in Formula 1 may be C; and X₃ and X₄ may beN, but they are not limited thereto.

B₁ to B₄ in Formula 1 may each independently be selected from a singlebond, O, and S.

For example, B₁ to B₄ in Formula 1 may be a single bond, but they arenot limited thereto.

Y₁ to Y₃ in Formula 1 may each independently be selected from a singlebond and a divalent linking group, and at least one selected from Y₁ toY₃ may be a divalent linking group.

For example, Y₁ and Y₂ may each be a single bond, and Y₃ may be adivalent linking group; or

Y₂ and Y₃ may each be a single bond, and Y₁ may be a divalent linkinggroup; or

Y₃ and Y₁ may each be a single bond, and Y₂ may be a divalent linkinggroup, but they are not limited thereto.

In an embodiment, regarding Formula 1, Y₁ and Y₂ may each be a divalentlinking group, and Y₃ may be a divalent single bond; or

Y₂ and Y₃ may each be a divalent linking group, and Y₁ may be a divalentsingle bond; or

Y₃ and Y₁ may each be a divalent linking group, and Y₂ may be a divalentsingle bond, but they are not limited thereto.

In an embodiment, Y₁ to Y₃ may be a divalent linking group, but they arenot limited thereto.

For example, regarding Formula 1, Y₁ to Y₃ may each independently beselected from a single bond and a divalent linking group, and at leastone selected from Y₁ to Y₃ may be a divalent linking group;

the divalent linking group may be selected from *—O—*′, *—S—*′,*—{B(R₈₁)}—*′, *—{N(R₈₁)}—*′, *—{C(R₈₁)(R₈₂)}_(n81)—*′,*—{Si(R₈₁)(R₈₂)}_(n81)—*′, a substituted or unsubstituted C₂-C₂₀alkenylene group, a substituted or unsubstituted C₂-C₂₀ alkynylenegroup, a substituted or unsubstituted C₆-C₂₀ arylene group, asubstituted or unsubstituted C₁-C₂₀ heteroarylene group, a substitutedor unsubstituted divalent non-aromatic condensed polycyclic group, and asubstituted or unsubstituted divalent non-aromatic condensedheteropolycyclic group;

R₈₁ and R₈₂ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a phenyl group, a naphthyl group, a pyridinylgroup, and a pyrimidinyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, and animidazopyridinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, and animidazopyridinyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a phenyl group, a naphthyl group, a fluorenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolylgroup, a thiophenyl group, a furanyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolylgroup, an indazolyl group, a purinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, an imidazopyridinyl group, and —Si(Q₁)(Q₂)(Q₃); and R₈₁ and R₈₂may optionally be linked to form a saturated or unsaturated ring;

Q₁ to Q₃ may each independently be selected from hydrogen, deuterium, aC₁-C₂₀ alkyl group, and a phenyl group;

n81 may be selected from 1, 2, 3, 4, and 5; and

* and *′ each independently indicate a binding site to a neighboringatom, but they are not limited thereto.

In an embodiment, Y₁ to Y₃ in Formula 1 may each independently beselected from a single bond and a divalent linking group, and at leastone selected from Y₁ to Y₃ may be a divalent linking group;

the divalent linking group may be selected from *—O—*′, *—S—*′,*—{B(R₈₁)}—*′, *—{N(R₈₁)}—*′, *—{C(R₈₁)(R₈₂)}_(n81)—*′,*—{Si(R₈₁)(R₈₂)}_(n81)—*′, a substituted or unsubstituted ethenylenegroup, a substituted or unsubstituted propenylene group, a substitutedor unsubstituted butenylene group, a substituted or unsubstitutedpentenylene group, a substituted or unsubstituted phenylene group, asubstituted or unsubstituted naphthylene group, a substituted orunsubstituted fluorenylene group, a substituted or unsubstitutedpyridinylene group, a substituted or unsubstituted pyrazinylene group, asubstituted or unsubstituted pyrimidinylene group, a substituted orunsubstituted quinolinylene group, a substituted or unsubstitutedisoquinolinylene group, a substituted or unsubstituted naphthyridinylenegroup, a substituted or unsubstituted quinoxalinylene group, asubstituted or unsubstituted quinazolinylene group, a substituted orunsubstituted dibenzofuranylene group, and a substituted orunsubstituted dibenzothiophenylene group;

R₈₁ and R₈₂ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a phenyl group, a naphthyl group, a pyridinylgroup, and a pyrimidinyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, and animidazopyridinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, and animidazopyridinyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂,—Si(CH₃)₃, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, afluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a pyrrolyl group, a thiophenyl group, a furanyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolylgroup, an indolyl group, an indazolyl group, a purinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, and an imidazopyridinyl group; and R₈₁and R₈₂ may optionally be linked to form a saturated or unsaturatedring;

n81 may be selected from 1, 2, 3, 4, and 5; and

* and *′ each independently indicate a binding site to a neighboringatom, but they are not limited thereto.

In an embodiment, Y₁ to Y₃ in Formula 1 may each independently beselected from a single bond and a divalent linking group, and at leastone selected from Y₁ to Y₃ may be a divalent linking group; and

the divalent linking group may be represented by one selected from*—O—*′, *—S—*′, and one of Formulae 8-1 to 8-18, but they are notlimited thereto:

In Formulae 8-1 to 8-18,

R₈₁ to R₈₈ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a phenyl group, a naphthyl group, a pyridinylgroup, and a pyrimidinyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, and animidazopyridinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, and animidazopyridinyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂,—Si(CH₃)₃, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, afluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a pyrrolyl group, a thiophenyl group, a furanyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolylgroup, an indolyl group, an indazolyl group, a purinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, and an imidazopyridinyl group;

n81 may be selected from 1, 2, 3, 4, and 5; and

* and *′ each independently indicate a binding site to a neighboringatom.

In an embodiment, R₈₁ to R₈₈ in Formulae 8-1 to 8-18 may eachindependently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, acyano group, a methyl group, an ethyl group, an n-propyl group, aniso-propyl group, an n-butyl group, an iso-butyl group, a sec-butylgroup, a tert-butyl group, a methoxy group, an ethoxy group, ann-propoxy group, an iso-propoxy group, an n-butoxy group, and atert-butoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, aphenyl group, and a naphthyl group;

a phenyl group, a naphthyl group, a pyridinyl group, and adibenzofuranyl group; and

a phenyl group, a naphthyl group, a pyridinyl group and a dibenzofuranylgroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, —Si(CH₃)₃, a cyanogroup, a methyl group, an ethyl group, an n-propyl group, an iso-propylgroup, an n-butyl group, an iso-butyl group, a sec-butyl group, atert-butyl group, a methoxy group, an ethoxy group, an n-propoxy group,an iso-propoxy group, n-butoxy group, tert-butoxy group, a phenyl group,a naphthyl group, and a pyridinyl group; and

n81 may be selected from 1 and 2, but they are not limited thereto.

In an embodiment, Y₁ to Y₃ in Formula 1 may each independently beselected from a single bond and a divalent linking group, at least oneselected from Y₁ to Y₃ is a divalent linking group; and

the divalent linking group may be represented by one selected from*—O—*′, *—S—*′, and one of Formulae 9-1 to 9-70, but they are notlimited thereto:

In Formulae 9-1 to 9-70,

Ph refers to a phenyl group;

2-pyr refers to a 2-pyridinyl group, 3-pyr refers to a 3-pyridinylgroup, 4-pyr refers to a 4-pyridinyl group; and

* and *′ each independently indicates a binding site to a neighboringatom.

Z₁ and Z₂ in Formula 1 may each independently be represented by one ofFormulae 2-1 to 2-4:

In Formulae 2-1 to 2-4,

Y₂₁ and Y₂₂ may each independently be selected from a substituted orunsubstituted C₁-C₁₀ alkylene group and a substituted or unsubstitutedC₂-C₁₀ alkenylene group;

a21 and a22 may each independently be selected from 0, 1, 2, 3, 4, and5;

R₂₁ to R₂₇ may each independently be selected from hydrogen, deuterium,a substituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₇-C₆₀ arylalkyl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group;

* indicates a binding site to a neighboring atom.

For example, in Formulae 2-1 to 2-4, Y₂₁ and Y₂₂ may each independentlybe selected from a methylene group, an ethylene group, and a propylenegroup; and

a methylene group, an ethylene group, and a propylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,—CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, and a C₁-C₂₀ alkyl group; and

a21 and a22 may each independently be selected from 0, 1, 2, and 3, butthey are not limited thereto.

In an embodiment, in Formulae 2-1 to 2-4, Y₂₁ and Y₂₂ may eachindependently be selected from a methylene group, an ethylene group, anda propylene group; and

a21 and a22 may each independently be selected from 0, 1, and 2, butthey are not limited thereto.

For example, in Formulae 2-1 to 2-4, R₂₁=R₂₂=R₂₃;

R₂₁≠R₂₂, and R₂₂≠R₂₃; or

R₂₁≠R₂₂, R₂₂≠R₂₃, and R₂₃≠R₂₁, but they are not limited thereto.

In an embodiment, in Formulae 2-1 to 2-4, R₂₁ to R₂₇ may eachindependently be selected from:

hydrogen, deuterium, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclooctyl group, an adamantanyl (adamantyl) group,a norbornanyl (norbornyl) group, a norbornenyl group, a cyclopentenylgroup, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, anaphthyl group, a pyridinyl group, and a pyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, an imidazopyridinyl group, and an imidazopyrimidinyl group; and

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, an imidazopyridinyl group, and an imidazopyrimidinyl group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,—CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclooctyl group, anadamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, and an imidazopyrimidinyl group, but they are not limitedthereto.

In an embodiment, R₂₁ to R₂₇ in Formulae 2-1 to 2-4 may eachindependently be selected from:

hydrogen, deuterium, a methyl group, an ethyl group, an n-propyl group,an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butylgroup, a tert-butyl group, an n-pentyl group, an iso-pentyl group, asec-pentyl group, and a tert-pentyl group;

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group,an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butylgroup, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, and atert-pentyl group, each substituted with at least one selected fromdeuterium and a phenyl group;

a phenyl group and a naphthyl group; and

a phenyl group and a naphthyl group, each substituted with at least oneselected from deuterium, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, aC₁-C₂₀ alkyl group, and a phenyl group, but they are not limitedthereto.

In an embodiment, R₂₁ to R₂₇ in Formulae 2-1 to 2-4 may eachindependently be selected from:

hydrogen, a methyl group, an ethyl group, an n-propyl group, aniso-propyl group, an n-butyl group, an iso-butyl group, a sec-butylgroup, a tert-butyl group, a phenyl group, and a naphthyl group, butthey are not limited thereto.

In an embodiment, in Formulae 2-1 and 2-2, R₂₁ and R₂₂ may eachindependently be selected from a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group; and

R₂₃ may be a substituted or unsubstituted C₁-C₆₀ alkyl group, but theyare not limited thereto.

In an embodiment, in Formulae 2-1 and 2-2, R₂₁ and R₂₂ may eachindependently be selected from a phenyl group, a naphthyl group, afluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a pyrrolyl group, a thiophenyl group, a furanyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolylgroup, an indolyl group, an indazolyl group, a purinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, an imidazopyridinyl group, and animidazopyrimidinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, and an imidazopyrimidinyl group, each substituted with at leastone selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃,—CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclooctyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthylgroup, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a pyrrolyl group, a thiophenyl group, a furanyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolylgroup, an indolyl group, an indazolyl group, a purinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, an imidazopyridinyl group, and animidazopyrimidinyl group; and

R₂₃ may be selected from a C₁-C₂₀ alkyl group; and

a C₁-C₂₀ alkyl group, substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctylgroup, an adamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinylgroup, but they are not limited thereto.

In an embodiment, in Formulae 2-1 and 2-2, R₂₁ and R₂₂ may eachindependently be selected from:

a phenyl group and a naphthyl group; and

a phenyl group and a naphthyl group, each substituted with at least oneselected from deuterium, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, aC₁-C₂₀ alkyl group, and a phenyl group; and

R₂₃ may be selected from a methyl group, an ethyl group, an n-propylgroup, an iso-propyl group, an n-butyl group, an iso-butyl group, asec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentylgroup, a sec-pentyl group, and a tert-pentyl group; and

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group,an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butylgroup, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, and atert-pentyl group, each substituted with at least one selected fromdeuterium and a phenyl group, but they are not limited thereto.

In an embodiment, in Formulae 2-1 and 2-2, R₂₁ and R₂₂ may eachindependently be selected from a phenyl group and a naphthyl group; and

R₂₃ may be selected from a methyl group, an ethyl group, an n-propylgroup, an iso-propyl group, an n-butyl group, an iso-butyl group, asec-butyl group, and a tert-butyl group, but they are not limitedthereto.

For example, Z₁ and Z₂ in Formula 1 may each independently berepresented by one of Formulae 2-11 to 2-20, but they are not limitedthereto:

In Formulae 2-11 to 2-20,

R₂₁ to R₂₃ may each independently be selected from a methyl group, anethyl group, an n-propyl group, an iso-propyl group, an n-butyl group,an iso-butyl group, a sec-butyl group, a tert-butyl group, a phenylgroup, and a naphthyl group; and

* indicates a binding site to a neighboring atom.

In an embodiment, in Formulae 2-11 to 2-20, R₂₁=R₂₂=R₂₃;

R₂₁=R₂₂, and R₂₂≠R₂₃; or

R₂₁≠R₂₂, R₂₂≠R₂₃, and R₂₃≠R₂₁, but they are not limited thereto.

In an embodiment, Z₁ and Z₂ in Formula 1 may each independently berepresented by one of Formulae 2-21 to 2-34, but they are not limitedthereto:

In Formulae 2-21 to 2-34,

Et refers to an ethyl group;

Ph refers to a phenyl group; and

* indicates a binding site to a neighboring atom.

In an embodiment, Z₁ and Z₂ in Formula 1 may each independently berepresented by one of Formulae 2-2 to 2-4, but they are not limitedthereto:

In Formulae 2-2 to 2-4,

Y₂₁, Y₂₂, a21, a22, and R₂₁ to R₂₇ are the same as described inconnection with Formulae 2-1 to 2-4.

In an embodiment, Z₁ and Z₂ in Formula 1 may each independently berepresented by one of Formulae 2-12 to 2-20, but they are not limitedthereto:

In Formulae 2-12 to 2-20,

R₂₁ to R₂₃ may each independently be selected from a methyl group, anethyl group, an n-propyl group, an iso-propyl group, an n-butyl group,an iso-butyl group, a sec-butyl group, a tert-butyl group, a phenylgroup, and a naphthyl group; and

* indicates a binding site to a neighboring atom.

In an embodiment, in Formulae 2-12 to 2-20, R₂₁=R₂₂=R₂₃;

R₂₁=R₂₂, and R₂₂≠R₂₃; or

R₂₁≠R₂₂, R₂₂≠R₂₃, and R₂₃≠R₂₁, but they are not limited thereto.

In an embodiment, Z₁ and Z₂ in Formula 1 may each independently berepresented by one of Formulae 2-26 to 2-34, but they are not limitedthereto:

In Formulae 2-26 to 2-34,

Et refers to an ethyl group;

Ph refers to a phenyl group; and

* indicates a binding site to a neighboring atom.

d1 in Formula 1 indicates the number of groups Z₁, and may be selectedfrom 0, 1, 2, 3, and 4. When d1 is 2 or more, groups Z₁ may be identicalto or different from each other.

d2 in Formula 1 indicates the number of groups Z₂, and may be selectedfrom 0, 1, 2, 3, and 4. When d2 is 2 or more, groups Z₂ may be identicalto or different from each other.

Regarding Formula 1, when X₃ is N, d1 may be selected from 1, 2, 3, and4; or when X₄ is N, d2 may be selected from 1, 2, 3, and 4.

For example, d1 and d2 in Formula 1 may each independently be selectedfrom 0, 1, and 2; and

at least one selected from d1 and d2 may be selected from 1 and 2, butthey are not limited thereto.

In an embodiment, d1 and d2 in Formula 1 may be 1, but they are notlimited thereto.

R₁ to R₄ in Formula 1 may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₇-C₆₀ arylalkyl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group, —C(═O)(Q₇),and —N(Q₇)(Q₈); R₁ and R₄ or R₂ and R₃ may optionally be linked to forma saturated or unsaturated ring,

wherein Q₇ and Q₈ may each independently be selected from a C₁-C₆₀ alkylgroup and a C₆-C₆₀ aryl group.

For example, R₁ to R₄ in Formula 1 may each independently be selectedfrom hydrogen, deuterium, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxygroup;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclooctyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthylgroup, a pyridinyl group, and a pyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, an imidazopyridinyl group, and an imidazopyrimidinyl group; and

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, an imidazopyridinyl group, and an imidazopyrimidinyl group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,—CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclooctyl group, anadamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, and an imidazopyrimidinyl group, but they are not limitedthereto.

In an embodiment, R₁ to R₄ in Formula 1 may each independently beselected from hydrogen, deuterium, a methyl group, an ethyl group, ann-propyl group, an iso-propyl group, an n-butyl group, an iso-butylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, aniso-pentyl group, a sec-pentyl group, and a tert-pentyl group;

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group,an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butylgroup, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, and atert-pentyl group, each substituted with at least one selected fromdeuterium and a phenyl group;

a phenyl group, a naphthyl group, and a carbazolyl group; and

a phenyl group, a naphthyl group, and a carbazolyl group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,—CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a C₁-C₂₀ alkyl group, a phenylgroup, and a naphthyl group, but they are not limited thereto.

In an embodiment, R₁ to R₄ in Formula 1 may each independently beselected from hydrogen, deuterium, a methyl group, an ethyl group, ann-propyl group, an iso-propyl group, an n-butyl group, an iso-butylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, aniso-pentyl group, a sec-pentyl group, and a tert-pentyl group; and

a phenyl group and a carbazolyl group; and

a phenyl group, a naphthyl group, and a carbazolyl group, eachsubstituted with at least one selected from a C₁-C₂₀ alkyl group and aphenyl group, but they are not limited thereto.

b1 in Formula 1 indicates the number of groups R₁, and b1 may beselected from 1, 2, 3, and 4. When b1 is 2 or more, groups R₁ may beidentical to or different from each other.

b2 in Formula 1 indicates the number of groups R₂, and b2 may beselected from 1, 2, 3, and 4. When b2 is 2 or more, groups R₂ may beidentical to or different from each other.

b3 in Formula 1 indicates the number of groups R₃, and b3 may beselected from 1, 2, 3, and 4. When b3 is 2 or more, groups R₃ may beidentical to or different from each other.

b4 in Formula 1 indicates the number of group R₄, and b4 may be selectedfrom 1, 2, 3, and 4. When b4 is 2 or more, groups R₄ may be identical toor different from each other.

L₁ in Formula 1 may be selected from a monodentate ligand and abidentate ligand.

Examples of the monodentate ligand include an iodide ion, a bromide ion,a chloride ion, a sulfide, a thiocyanate ion, a nitrate ion, an azideion, a hydroxide ion, a cyanide ion, an isocyanide ion, water, anacetonitrile, a pyridine, an ammonia, a carbon monoxide, PPh₃, PPh₂CH₃,PPh(CH₃)₂, and P(CH₃)₃, but they are not limited thereto.

Examples of the bidentate ligand include an oxalate ion,acetylacetonate, a picolinic acid, 2-(2-hydroxyphenyl)-pyridine,2-phenylpyridine, 1,2-bis(diphenylphosphino)ethane (dppe),1,1-bis(diphenylphosphino)methane (dppm), glycinate, ethylenediamine,2,2′-bipyridine, and 1,10-phenanthroline, but they are not limitedthereto.

For example, L₁ in Formula 1 may be represented by one of Formulae 3-1to 3-6, but they are not limited thereto:

In Formulae 3-1 to 3-6,

A₃₁ may be selected from a C₅-C₂₀ carbocyclic group and a C₁-C₂₀heterocyclic group;

X₃₁ and X₃₂ may each independently be selected from C and N;

Y₃₁ may be selected from a single bond, a carbon-carbon double bond, asubstituted or unsubstituted C₁-C₅ alkylene group, a substituted orunsubstituted C₂-C₅ alkenylene group, and a substituted or unsubstitutedC₆-C₁₀ arylene group;

Z₃₁ and Z₃₂ may each independently be selected from N, O, N(R₃₄),P(R₃₄)(R₃₅), and As(R₃₄)(R₃₅);

Z₃₃ may be selected from P and As;

R₃₁ to R₃₅ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₇-C₆₀ arylalkyl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryl group, a substituted or unsubstituted C₁-C₆₀heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group;

b31 may be selected from 1, 2, and 3; and

* and *′ may each independently indicate a binding site to a neighboringatom.

For example, A₃₁ in Formulae 3-1 to 3-6 may be selected from a benzenegroup, a naphthalene group, a pyridine group, a pyrimidine group, atriazine group, a quinoline group, and an isoquinoline group, but is notlimited thereto.

For example, Y₃₁ in Formulae 3-1 to 3-6 may be selected from asubstituted or unsubstituted methylene group and a substituted orunsubstituted phenylene group, but is not limited thereto.

For example, Z₃₃ in Formulae 3-1 to 3-6 may be P, but is not limitedthereto.

For example, R₃₁ to R₃₅ in Formulae 3-1 to 3-6 may each independently beselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxygroup;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a phenyl group, a naphthyl group, a pyridinylgroup, and a pyrimidinyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, and animidazopyridinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, and animidazopyridinyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a phenyl group, a naphthyl group, a fluorenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolylgroup, a thiophenyl group, a furanyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolylgroup, an indazolyl group, a purinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, and an imidazopyridinyl group, but they are not limited thereto.

In an embodiment, U in Formula 1 may be represented by one of Formulae4-1 to 4-5, but is not limited thereto:

In Formulae 4-1 to 4-5,

Ph refers to a phenyl group; and

* and *′ may each indicate a binding site to a neighboring atom.

a1 in Formula 1 indicates the number of groups L₁, and a1 may beselected from 0, 1, and 2. When a1 is 2 or more, groups U may beidentical to or different from each other.

For example, a1 in Formula 1 may be 0, but is not limited thereto.

In an embodiment, in Formula 1, M may be Pt, and a1 may be 0, but theyare not limited thereto.

In an embodiment, in Formula 1, M may be Os, and a1 may be 2, but theyare not limited thereto.

The organometallic compound represented by Formula 1 may be representedby one of Formulae 1-1 to 1-3, but the formula representing theorganometallic compound is not limited thereto:

In Formulae 1-1 to 1-3,

M, A₁ to A₄, X₁ to X₄, Z₁, Z₂, d1, d2, R₁ to R₄, b1 to b4, L₁, and a1are the same as described above in connection with Formula 1; and

Y₁ to Y₃ may each independently indicate a divalent linking group.

For example, in Formulae 1-1 to 1-3, M is selected from Ir, Pt, and Os;

A₁ to A₄ may each independently be selected from a benzene group, anaphthalene group, a pyridine group, a pyrimidine group, a quinolinegroup, and an isoquinoline group;

at least one selected from A₃ and A₄ may be selected from a pyridinegroup, a pyrimidine group, a quinoline group, and an isoquinoline group;

X₁ and X₂ may be C;

X₃ and X₄ may each independently be selected from C and N, and at leastone selected from X₃ and X₄ may be N, but they are not limited thereto.

The organometallic compound represented by Formula 1 may be representedby one of Formulae 1-11 to 1-13, but the formula representing theorganometallic compound is not limited thereto:

In Formulae 1-11 to 1-13,

M, A₁ to A₄, X₁ to X₃, Z₁; Z₂, R₁ to R₄, b1 to b4, L₁; and a1 are thesame as described above in connection with Formula 1;

Y₁ to Y₃ may each independently be a divalent linking group;

d1 may be selected from 0, 1, 2, 3, and 4; and

d2 may be selected from 1, 2, 3, and 4.

For example, Z₁ and Z₂ in Formulae 1-11 to 1-13 may each independentlybe represented by one of Formulae 2-21 to 2-34, but they are not limitedthereto.

In an embodiment, in Formulae 1-11 to 1-13, M is Pt, and a1 is 0, butthey are not limited thereto.

The organometallic compound represented by Formula 1 may be representedby one of Formulae 1-14 to 1-16, but the formula representing theorganometallic compound is not limited thereto:

In Formulae 1-14 to 1-16,

M, A₁ to A₄, X₁, X₂, X₄, Z₁, Z₂, R₁ to R₄, b1 to b4, L₁, and a1 are thesame as described above in connection with Formula 1;

Y₁ to Y₃ may each independently be a divalent linking group;

d1 may be selected from 1, 2, 3, and 4; and

d2 may be selected from 0, 1, 2, 3, and 4.

For example, Z₁ and Z₂ in Formulae 1-14 to 1-16 may each independentlybe represented by one of Formulae 2-21 to 2-34, but they are not limitedthereto.

In an embodiment, in Formulae 1-14 to 1-16, M is Pt, and a1 is 0, butthey are not limited thereto.

The organometallic compound represented by Formula 1 may be representedby one of Formulae 1-17 to 1-19, but the formula representing theorganometallic compound is not limited thereto:

In Formulae 1-17 to 1-19,

M, A₁ to A₄, X₁, X₂, Z₁, Z₂, R₁ to R₄, b1 to b4, L₁, and a1 are the sameas described above in connection with Formula 1;

Y₁ to Y₃ may each independently be a divalent linking group;

d1 may be selected from 1, 2, 3, and 4; and

d2 may be selected from 1, 2, 3, and 4.

For example, Z₁ and Z₂ in Formulae 1-17 to 1-19 may each independentlybe represented by one of Formulae 2-21 to 2-34, but they are not limitedthereto.

In an embodiment, in Formulae 1-17 to 1-19, M is Pt, and a1 is 0, butthey are not limited thereto.

The organometallic compound represented by Formula 1 may be selectedfrom Compounds 1 to 18 and 20 to 37, but the formula representing theorganometallic compound is not limited thereto:

In Compounds 1 to 18 and 20 to 37,

TMS refers to a trimethylsilyl group.

In the organometallic compound represented by Formula 1, as illustratedin Formula 1′, an N-containing ring may be necessarily substituted witha group represented by one of Formulae 2-1 to 2-4.

When the N-containing ring is substituted with the group represented byone of Formulae 2-1 to 2-4, an empty d-orbital of Si or Ge can be filledwith electrons. Accordingly, since the N-containing ring is substitutedwith the group represented by one of Formulae 2-1 to 2-4, when electronsand/or energy flow or are applied to the organometallic compoundrepresented by Formula 1, the chemical, physical, and/or electricstability of the organometallic compound represented by Formula 1 may beimproved. Thus, the lifespan of an organic light-emitting deviceincluding the organometallic compound represented by Formula 1 may beincreased.

Due to the introduction of the group represented by one of Formulae 2-1to 2-4 in the organometallic compound represented by Formula 1, sterichindrance may be increased, and the organometallic compound representedby Formula 1 may have a non-planar structure. Since the organometalliccompound represented by Formula 1 has a non-planar structure, lessaggregation may occur, and the efficiency of an organic light-emittingdevice including the organometallic compound represented by Formula 1may be improved.

Synthesis methods of the organometallic compound represented by Formula1 may be recognizable by one of ordinary skill in the art by referringto Synthesis Examples provided below.

The organometallic compound represented by Formula 1 is suitable for usein an organic layer of an organic light-emitting device, for example,for use as a dopant in an emission layer of the organic layer. Thus,another aspect provides an organic light-emitting device that includes:

a first electrode;

a second electrode; and

an organic layer that is disposed between the first electrode and thesecond electrode,

wherein the organic layer includes an emission layer and at least oneorganometallic compound represented by Formula 1.

The organometallic compound of Formula 1 may be used between a pair ofelectrodes of an organic light-emitting device. For example, theorganometallic compound represented by Formula 1 may be included in theemission layer. In this regard, the organometallic compound may act as adopant, and the emission layer may further include a host (that is, anamount of the organometallic compound represented by Formula 1 issmaller than an amount of the host).

The expression that “(an organic layer) includes at least one oforganometallic compounds” as used herein may include an embodiment inwhich “(an organic layer) includes identical organometallic compoundsrepresented by Formula 1” and an embodiment in which “(an organic layer)includes two or more different organometallic compounds represented byFormula 1.”

For example, the organic layer may include only Compound 1 as theorganometallic compound. In this regard, Compound 1 may be included onlyin the emission layer of the organic light-emitting device. In otherembodiments, the organic layer may include, as the organometalliccompound, Compound 1 and Compound 2. In those embodiments, Compound 1and Compound 2 may be included in an identical layer (for example,Compound 1 and Compound 2 all may be included in an emission layer).

The first electrode may be an anode, which is a hole injectionelectrode, and the second electrode may be a cathode, which is anelectron injection electrode; or the first electrode may be a cathode,which is an electron injection electrode, and the second electrode maybe an anode, which is a hole injection electrode.

For example, the first electrode may be an anode, and the secondelectrode may be a cathode, and the organic layer may include:

i) a hole transport region disposed between the first electrode and theemission layer, wherein the hole transport region includes at least oneselected from a hole injection layer, a hole transport layer, and anelectron blocking layer, and

ii) an electron transport region disposed between the emission layer andthe second electrode, wherein the electron transport region includes atleast one selected from a hole blocking layer, an electron transportlayer, and an electron injection layer.

FIG. 1 is a schematic view of an organic light-emitting device 10according to an embodiment. Hereinafter, the structure of an organiclight-emitting device according to an embodiment and a method ofmanufacturing an organic light-emitting device according to anembodiment will be described in connection with FIG. 1. The organiclight-emitting device 10 includes a first electrode 11, an organic layer15, and a second electrode 19, which are sequentially stacked.

A substrate may be additionally disposed under the first electrode 11 orabove the second electrode 19. For use as the substrate, any substratethat is used in general organic light-emitting devices may be used here,and the substrate may be a glass substrate or a transparent plasticsubstrate, each having excellent mechanical strength, thermal stability,transparency, surface smoothness, ease of handling, andwater-resistance.

The first electrode 11 may be formed by depositing or sputtering amaterial for forming the first electrode 11 on the substrate. The firstelectrode 11 may be an anode. The material for forming the firstelectrode 11 may be selected from materials with a high work function tofacilitate hole injection. The first electrode 11 may be a reflectiveelectrode, a semi-transmissive electrode, or a transmissive electrode.The material for forming the first electrode may be, for example, indiumtin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), and zincoxide (ZnO). In some embodiments, magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), ormagnesium-silver (Mg—Ag) may be used as the material for forming thefirst electrode.

The first electrode 11 may have a single-layered structure or amulti-layered structure including two or more layers. For example, thefirst electrode 11 may have a three-layered structure of ITO/Ag/ITO, butthe structure of the first electrode 11 is not limited thereto.

The organic layer 15 is disposed on the first electrode 11.

The organic layer 15 may include a hole transport region, an emissionlayer, and an electron transport region.

The hole transport region may be disposed between the first electrode 11and the emission layer.

The hole transport region may include at least one selected from a holeinjection layer, a hole transport layer, an electron blocking layer, anda buffer layer.

The hole transport region may include only either a hole injection layeror a hole transport layer. In some embodiments, the hole transportregion may have a structure of hole injection layer/hole transport layeror hole injection layer/hole transport layer/electron blocking layer,which are sequentially stacked in this stated order from the firstelectrode 11.

A hole injection layer may be formed on the first electrode 11 by usingone or more suitable methods selected from vacuum deposition, spincoating, casting, or Langmuir-Blodgett (LB) deposition.

When a hole injection layer is formed by vacuum deposition, thedeposition conditions may vary according to a material that is used toform the hole injection layer, and the structure and thermalcharacteristics of the hole injection layer. For example, the depositionconditions may include a deposition temperature of about 100 to about500° C., a vacuum pressure of about 10⁻⁸ to about 10⁻³ torr, and adeposition rate of about 0.01 to about 100 Å/sec. However, thedeposition conditions are not limited thereto.

When the hole injection layer is formed using spin coating, coatingconditions may vary according to the material used to form the holeinjection layer, and the structure and thermal properties of the holeinjection layer. For example, a coating speed may be from about 2,000revolutions per minute (rpm) to about 5,000 rpm, and a temperature atwhich a heat treatment is performed to remove a solvent after coatingmay be from about 80° C. to about 200° C. However, the coatingconditions are not limited thereto.

Conditions for forming a hole transport layer and an electron blockinglayer may be understood by referring to conditions for forming the holeinjection layer.

The hole transport region may include at least one selected fromm-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB,methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine(TCTA), polyaniline/dodecylbenzene sulfonic acid (Pani/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (Pani/CSA),polyaniline/poly(4-styrenesulfonate) (Pani/PSS), a compound representedby Formula 201 below, and a compound represented by Formula 202 below:

Ar₁₀₁ and Ar₁₀₂ in Formula 201 may each independently be selected from:

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anacenaphthylene group, a fluorenylene group, a phenalenylene group, aphenanthrenylene group, an anthracenylene group, a fluoranthenylenegroup, a triphenylenylene group, a pyrenylene group, a chrysenylenylenegroup, a naphthacenylene group, a picenylene group, a perylenylenegroup, and a pentacenylene group; and

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anacenaphthylene group, a fluorenylene group, a phenalenylene group, aphenanthrenylene group, an anthracenylene group, a fluoranthenylenegroup, a triphenylenylene group, a pyrenylene group, a chrysenylenylenegroup, a naphthacenylene group, a picenylene group, a perylenylenegroup, and a pentacenylene group, each substituted with at least oneselected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₇-C₆₀ arylalkyl group, a C₁-C₆₀ heteroarylgroup, a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, aC₂-C₆₀ heteroarylalkyl group, a monovalent non-aromatic condensedpolycyclic group, and a monovalent non-aromatic condensedheteropolycyclic group.

xa and xb in Formula 201 may each independently be an integer selectedfrom 0 to 5, or 0, 1, or 2. For example, xa is 1 and xb is 0, but xa andxb are not limited thereto.

R₁₀₁ to R₁₀₈, R₁₁₁ to R₁₁₉, and R₁₂₁ to R₁₂₄ in Formulae 201 and 202 mayeach independently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₁₀ alkyl group (for example, a methyl group, an ethyl group, apropyl group, a butyl group, pentyl group, a hexyl group, etc.), and aC₁-C₁₀ alkoxy group (for example, a methoxy group, an ethoxy group, apropoxy group, butoxy group, a pentoxy group, etc.);

a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, and a phosphoric acidgroup or a salt thereof;

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenylgroup, and a pyrenyl group; and

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenylgroup, and a pyrenyl group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₁₀ alkyl group, and a C₁-C₁₀ alkoxy group, but they are notlimited thereto.

R₁₀₉ in Formula 201 may be selected from:

a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinylgroup; and

a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinylgroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, ananthracenyl group, and a pyridinyl group.

In an embodiment, the compound represented by Formula 201 may berepresented by Formula 201A, but the formula representing the compoundis not limited thereto:

R₁₀₁, R₁₁₁, R₁₁₂, and R₁₀₉ in Formula 201A may be understood byreferring to the description provided herein.

For example, the compound represented by Formula 201, and the compoundrepresented by Formula 202 may include compounds HT1 to HT20 illustratedbelow, but are not limited thereto:

A thickness of the hole transport region may be in a range of about 100Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When thehole transport region includes a hole injection layer and a holetransport layer, the thickness of the hole injection layer may be in arange of about 100 Å to about 10,000 Å, and for example, about 100 Å toabout 1,000 Å, and the thickness of the hole transport layer may be in arange of about 50 Å to about 2,000 Å, and for example, about 100 Å toabout 1,500 Å. While not wishing to be bound by theory, it is understoodthat when the thicknesses of the hole transport region, the holeinjection layer and the hole transport layer are within these ranges,satisfactory hole transporting characteristics may be obtained without asubstantial increase in driving voltage.

The hole transport region may further include, in addition to thesematerials, a charge-generation material for the improvement ofconductive properties. The charge-generation material may behomogeneously or non-homogeneously dispersed in the hole transportregion.

The charge-generation material may be, for example, a p-dopant. Thep-dopant may be one selected from a quinone derivative, a metal oxide,and a cyano group-containing compound, but embodiments are not limitedthereto. Non-limiting examples of the p-dopant include a quinonederivative, such as tetracyanoquinonedimethane (TCNQ) or2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F₄-TCNQ); ametal oxide, such as a tungsten oxide or a molybdenium oxide; and acyano group-containing compound, such as Compound HT-D1 below, but arenot limited thereto.

The hole transport region may include a buffer layer.

Also, the buffer layer may compensate for an optical resonance distanceaccording to a wavelength of light emitted from the emission layer, andthus, efficiency of a formed organic light-emitting device may beimproved.

Then, an emission layer may be formed on the hole transport region byvacuum deposition, spin coating, casting, LB deposition, or the like.When the emission layer is formed by vacuum deposition or spin coating,the deposition or coating conditions may be similar to those applied toform the hole injection layer although the deposition or coatingconditions may vary according to the material that is used to form theemission layer.

Meanwhile, when the hole transport region includes an electron blockinglayer, a material for the electron blocking layer may be selected frommaterials for the hole transport region described above and materialsfor a host to be explained later. However, the material for the electronblocking layer is not limited thereto. For example, when the holetransport region includes an electron blocking layer, a material for theelectron blocking layer may be mCP, which will be explained later.

The emission layer may include a host and a dopant, and the dopant mayinclude the organometallic compound represented by Formula 1.

The host may include at least one selected from TPBi, TBADN, ADN (alsoreferred to as “DNA”), CBP, CDBP, TCP, mCP, Compound H50, and CompoundH51:

In some embodiments, the host may further include a compound representedby Formula 301 below.

Ar₁₁₁ and Ar₁₁₂ in Formula 301 may each independently be selected from:

a phenylene group, a naphthylene group, a phenanthrenylene group, and apyrenylene group; and

a phenylene group, a naphthylene group, a phenanthrenylene group, and apyrenylene group, each substituted with at least one selected from aphenyl group, a naphthyl group, and an anthracenyl group.

Ar₁₁₃ to Ar₁₁₆ in Formula 301 may each independently be selected from:

a C₁-C₁₀ alkyl group, a phenyl group, a naphthyl group, a phenanthrenylgroup, and a pyrenyl group; and

a phenyl group, a naphthyl group, a phenanthrenyl group, and a pyrenylgroup, each substituted with at least one selected from a phenyl group,a naphthyl group, and an anthracenyl group.

g, h, i, and j in Formula 301 may each independently be an integerselected from 0 to 4, and may be, for example, 0, 1, or 2.

Ar₁₁₃ to Ar₁₁₆ in Formula 301 may each independently be selected from:

a C₁-C₁₀ alkyl group, substituted with at least one selected from aphenyl group, a naphthyl group, and an anthracenyl group;

a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl, aphenanthrenyl group, and a fluorenyl group;

a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group,a phenanthrenyl group, and a fluorenyl group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a phenyl group, a naphthylgroup, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, anda fluorenyl group; and

but embodiments are not limited thereto.

In some embodiments, the host may include a compound represented byFormula 302:

Ar₁₂₂ to Ar₁₂₅ in Formula 302 are the same as described in detail inconnection with Ar₁₁₃ in Formula 301.

Ar₁₂₆ and Ar₁₂₇ in Formula 302 may each independently be a C₁-C₁₀ alkylgroup (for example, a methyl group, an ethyl group, or a propyl group).

k and l in Formula 302 may each independently be an integer selectedfrom 0 to 4. For example, k and l may each be 0, 1, or 2.

The compound represented by Formula 301 and the compound represented byFormula 302 may include Compounds H1 to H42 illustrated below, but arenot limited thereto:

When the organic light-emitting device is a full color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, and a blue emission layer. Insome embodiments, due to a stack structure including a red emissionlayer, a green emission layer, and/or a blue emission layer, theemission layer may emit white light.

When the emission layer includes a host and a dopant, an amount of thedopant may be in a range of about 0.01 to about 15 parts by weight basedon 100 parts by weight of the host, but is not limited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. While notwishing to be bound by theory, it is understood that when the thicknessof the emission layer is within this range, excellent light-emissioncharacteristics may be obtained without a substantial increase indriving voltage.

Then, an electron transport region may be disposed on the emissionlayer.

The electron transport region may include at least one selected from ahole blocking layer, an electron transport layer, and an electroninjection layer.

For example, the electron transport region may have a structure of holeblocking layer/electron transport layer/electron injection layer or astructure of electron transport layer/electron injection layer, but thestructure of the electron transport region is not limited thereto. Theelectron transport layer may have a single-layered structure or amulti-layered structure including two or more different materials.

Conditions for forming the hole blocking layer, the electron transportlayer, and the electron injection layer which constitute the electrontransport region may be understood by referring to the conditions forforming the hole injection layer.

When the electron transport region includes a hole blocking layer, thehole blocking layer may include, for example, at least one of BCP,Bphen, and BAlq but is not limited thereto:

A thickness of the hole blocking layer may be in a range of about 20 Åto about 1,000 Å, for example, about 30 Å to about 300 Å. While notwishing to be bound by theory, it is understood that when the thicknessof the hole blocking layer is within these ranges, the hole blockinglayer may have improved hole blocking ability without a substantialincrease in driving voltage.

The electron transport layer may further include at least one selectedfrom BCP, Bphen, Alq₃, BAlq, TAZ, and NTAZ:

In some embodiments, the electron transport layer may include at leastone of ET1 and ET2, but are not limited thereto:

A thickness of the electron transport layer may be in a range of about100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Whilenot wishing to be bound by theory, it is understood that when thethickness of the electron transport layer is within the range describedabove, the electron transport layer may have satisfactory electrontransport characteristics without a substantial increase in drivingvoltage.

Also, the electron transport layer may further include, in addition tothe materials described above, a metal-containing material.

The metal-containing material may include a Li complex. The Li complexmay include, for example, Compound ET-D1 (lithium quinolate, LiQ) orET-D2.

The electron transport region may include an electron injection layer(EIL) that promotes flow of electrons from the second electrode 19thereinto.

The electron injection layer may include at least one selected from,LiF, NaCl, CsF, Li₂O, BaO, and LiQ.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, for example, about 3 Å to about 90 Å. While notwishing to be bound by theory, it is understood that when the thicknessof the electron injection layer is within the range described above, theelectron injection layer may have satisfactory electron injectioncharacteristics without a substantial increase in driving voltage.

The second electrode 19 is disposed on the organic layer 15. The secondelectrode 19 may be a cathode. A material for forming the secondelectrode 19 may be selected from metal, an alloy, an electricallyconductive compound, and a combination thereof, which have a relativelylow work function. For example, lithium (Li), magnesium (Mg), aluminum(Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In),or magnesium-silver (Mg—Ag) may be used as a material for forming thesecond electrode 19. In some embodiments, to manufacture a top emissiontype light-emitting device, a transmissive electrode formed using ITO orIZO may be used as the second electrode 19.

Hereinbefore, the organic light-emitting device has been described withreference to FIG. 1, but is not limited thereto.

The term “C₁-C₆₀ alkyl group” as used herein refers to a linear orbranched aliphatic saturated hydrocarbon monovalent group having 1 to 60carbon atoms, and examples thereof include a methyl group, an ethylgroup, a propyl group, an iso-butyl group, a sec-butyl group, atert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group.The term “C₁-C₆₀ alkylene group” as used herein refers to a divalentgroup having the same structure as the C₁-C₆₀ alkyl group.

The term “C₁-C₆₀ alkoxy group” as used herein refers to a monovalentgroup represented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group),and non-limiting examples thereof include a methoxy group, an ethoxygroup, and an iso-propyloxy group.

The term “C₂-C₆₀ alkenyl group” as used herein refers to a hydrocarbongroup formed by including at least one carbon-carbon double bond in themiddle or at the terminus of the C₂-C₆₀ alkyl group, and examplesthereof include an ethenyl group, a propenyl group, and a butenyl group.The term “C₂-C₆₀ alkenylene group” as used herein refers to a divalentgroup having the same structure as the C₂-C₆₀ alkenyl group.

The term “C₂-C₆₀ alkynyl group” as used herein refers to a hydrocarbongroup formed by including at least one carbon-carbon triple bond in themiddle or at the terminus of the C₂-C₆₀ alkyl group, and examplesthereof include an ethynyl group, and a propynyl group. The term “C₂-C₆₀alkynylene group” as used herein refers to a divalent group having thesame structure as the C₂-C₆₀ alkynyl group.

The term “C₃-C₁₀ cycloalkyl group” as used herein refers to a monovalentsaturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, andnon-limiting examples thereof include a cyclopropyl group, a cyclobutylgroup, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.The term “C₃-C₁₀ cycloalkylene group” as used herein refers to adivalent group having the same structure as the C₃-C₁₀ cycloalkyl group.

The term “C₁-C₁₀ heterocycloalkyl group” as used herein refers to amonovalent monocyclic group having at least one heteroatom selected fromN, O, P, and S as a ring-forming atom and 1 to 10 carbon atoms, andexamples thereof include a tetrahydrofuranyl group, and atetrahydrothiophenyl group. The term “C₁-C₁₀ heterocycloalkylene group”as used herein refers to a divalent group having the same structure asthe C₁-C₁₀ heterocycloalkyl group.

The term “C₃-C₁₀ cycloalkenyl group” as used herein refers to amonovalent monocyclic group that has 3 to 10 carbon atoms and at leastone carbon-carbon double bond in the ring thereof, and which is notaromatic, and examples thereof include a cyclopentenyl group, acyclohexenyl group, and a cycloheptenyl group. The term “C₃-C₁₀cycloalkenylene group” as used herein refers to a divalent group havingthe same structure as the C₃-C₁₀ cycloalkenyl group.

The term “C₁-C₁₀ heterocycloalkenyl group” as used herein refers to amonovalent monocyclic group that has at least one heteroatom selectedfrom N, O, P, and S as a ring-forming atom, 1 to 10 carbon atoms, and atleast one carbon-carbon double bond in its ring. Non-limiting examplesof the C₁-C₁₀ heterocycloalkenyl group include a 2,3-dihydrofuranylgroup and a 2,3-dihydrothiophenyl group. The term “C₁-C₁₀heterocycloalkenylene group” as used herein refers to a divalent grouphaving the same structure as the C₁-C₁₀ heterocycloalkenyl group.

The term “C₆-C₆₀ aryl group” as used herein refers to a monovalent grouphaving a carbocyclic aromatic system having 6 to 60 carbon atoms, and aC₆-C₆₀ arylene group as used herein refers to a divalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms. Non-limitingexamples of the C₆-C₆₀ aryl group include a phenyl group, a naphthylgroup, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, anda chrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀ arylenegroup each include two or more rings, the rings may be fused to eachother.

The term “C₁-C₆₀ heteroaryl group” as used herein refers to a monovalentgroup having an aromatic system that has at least one heteroatomselected from N, O, P, and S as a ring-forming atom, and 1 to 60 carbonatoms. A C₁-C₆₀ heteroarylene group as used herein refers to a divalentgroup having a carbocyclic aromatic system that has at least oneheteroatom selected from N, O, P, and S as a ring-forming atom, and 1 to60 carbon atoms. Non-limiting examples of the C₁-C₆₀ heteroaryl groupinclude a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyl group, a triazinyl group, a quinolinyl group, and anisoquinolinyl group. When the C₁-C₆₀ heteroaryl group and the C₁-C₆₀heteroarylene group each include two or more rings, the rings may befused to each other.

The term “C₆-C₆₀ aryloxy group” as used herein indicates —OA₁₀₂ (whereinA₁₀₂ is the C₆-C₆₀ aryl group), the term “C₆-C₆₀ arylthio group” as usedherein indicates —SA₁₀₃ (wherein A₁₀₃ is the C₆-C₆₀ aryl group), and theterm “C₇-C₆₀ arylalkyl group” as used herein indicates -A₁₀₄A₁₀₅(wherein A₁₀₅ is the C₆-C₅₉ aryl group and A₁₀₄ is the C₁-C₅₃ alkylenegroup).

The term “C₂-C₆₀ heteroaryloxy group” as used herein indicates —OA₁₀₆(wherein A₁₀₆ is the C₂-C₆₀ heteroaryl group), the term “C₂-C₆₀heteroarylthio group” as used herein indicates —SA₁₀₇ (wherein A₁₀₇ isthe C₂-C₆₀ heteroaryl group), and the term “C₃-C₆₀ heteroarylalkylgroup” as used herein indicates -A₁₀₈A₁₀₉ (wherein A₁₀₉ is the C₁-C₅₉heteroaryl group and A₁₀₈ is the C₁-C₅₉ alkylene group).

The term “monovalent non-aromatic condensed polycyclic group” as usedherein refers to a monovalent group (for example, having 8 to 60 carbonatoms) that has two or more rings condensed to each other, only carbonatoms as a ring-forming atom, and which is non-aromatic in the entiremolecular structure. Examples of the monovalent non-aromatic condensedpolycyclic group include a fluorenyl group. The term “divalentnon-aromatic condensed polycyclic group” as used herein refers to adivalent group having the same structure as the monovalent non-aromaticcondensed polycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” asused herein refers to a monovalent group (for example, having 2 to 60carbon atoms) that has two or more rings condensed to each other, has aheteroatom selected from N, O, P, and S, other than carbon atoms, as aring-forming atom, and which is non-aromatic in the entire molecularstructure. Non-limiting examples of the monovalent non-aromaticcondensed heteropolycyclic group include a carbazolyl group. The term“divalent non-aromatic condensed heteropolycyclic group” as used hereinrefers to a divalent group having the same structure as the monovalentnon-aromatic condensed heteropolycyclic group.

As used herein, at least one substituent selected from the substitutedC₁-C₆₀ alkyl group, substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀alkynyl group, substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀cycloalkyl group, substituted C₁-C₁₀ heterocycloalkyl group, substitutedC₃-C₁₀ cycloalkenyl group, substituted C₁-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₇-C₆₀ arylalkyl group,substituted C₁-C₆₀ heteroaryl group, substituted C₁-C₆₀ heteroaryloxygroup, substituted C₁-C₆₀ heteroarylthio group, substituted C₂-C₆₀heteroarylalkyl group, substituted monovalent non-aromatic condensedpolycyclic group, and substituted monovalent non-aromatic condensedheteropolycyclic group may be selected from:

deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H,—CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₇-C₆₀ arylalkyl group, a C₁-C₆₀ heteroarylgroup, a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, aC₂-C₆₀ heteroarylalkyl group, a monovalent non-aromatic condensedpolycyclic group, and a monovalent non-aromatic condensedheteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀arylalkyl group, a C₁-C₆₀ heteroaryl group, a C₁-C₆₀ heteroaryloxygroup, a C₁-C₆₀ heteroarylthio group, a C₂-C₆₀ heteroarylalkyl group, amonovalent non-aromatic condensed polycyclic group, and a monovalentnon-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀arylalkyl group, a C₁-C₆₀ heteroaryl group, a C₁-C₆₀ heteroaryloxygroup, a C₁-C₆₀ heteroarylthio group, a C₂-C₆₀ heteroarylalkyl group, amonovalent non-aromatic condensed polycyclic group, and a monovalentnon-aromatic condensed heteropolycyclic group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂,—CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxygroup, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀arylalkyl group, a C₁-C₆₀ heteroaryl group, a C₁-C₆₀ heteroaryloxygroup, a C₁-C₆₀ heteroarylthio group, a C₂-C₆₀ heteroarylalkyl group, amonovalent non-aromatic condensed polycyclic group, and a monovalentnon-aromatic condensed heteropolycyclic group; and

—C(═O)(Q₁₁), —Si(Q₁₁)(Q₁₂)(Q₁₃), and —N(Q₁₁)(Q₁₂),

wherein Q₁₁ to Q₁₃ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₇-C₆₀ arylalkyl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.

When a group containing a specified number of carbon atoms issubstituted with any of the groups listed in the preceding paragraphs,the number of carbon atoms in the resulting “substituted” group isdefined as the sum of the carbon atoms contained in the original(unsubstituted) group and the carbon atoms (if any) contained in thesubstituent. For example, when the term “substituted C₁-C₆₀ alkyl”refers to a C₁-C₆₀ alkyl group substituted with C₆-C₆₀ aryl group, thetotal number of carbon atoms in the resulting aryl substituted alkylgroup is C₇-C₁₂₀.

Hereinafter, a compound and an organic light-emitting device accordingto embodiments are described in detail with reference to SynthesisExample and Examples. However, the organic light-emitting device is notlimited thereto. Referring to Synthesis Examples, the expression “‘B’ isused instead of ‘A’” means that the amount of ‘B’ is identical to theamount of ‘A’ in terms of a molar equivalent.

EXAMPLES Synthesis Example 1 Synthesis of Compound 3

Synthesis of Intermediate I-3-2

15.0 grams (g) (74.7 millimoles, mmol) of 3-bromophenylboronic acid, 165milliliters (ml) of toluene, and 60 ml of ethanol were added to areactor. Then, 13.2 g (57.5 mmol) of 2-bromo-5-(trimethylsilyl)pyridine, 4.6 g (4.02 mmol) of Pd(PPh₃)₄, and 60 ml of 2.0 molar (M)sodium carbonate solution were added thereto, and the mixture was heatedunder reflux at a temperature of 110° C. for 18 hours. Once the reactionwas completed, the mixture was condensed under reduced pressure, andthen, dissolved in 400 ml of dichloromethane. The resultant was filteredthrough diatomite. An organic layer obtained therefrom was dried byusing magnesium sulfate and distilled under reduced pressure, followedby purification by liquid chromatography, thereby completing thepreparation of 14.2 g (46 mmol, yield of 80%) of Intermediate I-3-2.

LC-MS m/z=306 (M+H)⁺

2) Synthesis of Intermediate I-3-1

8.5 g (27.6 mmol) of Intermediate I-3-2 and 250 ml of toluene were addedto a reactor. 1.56 ml (11.1 mmol) of 2,4,6-trimethylaniline, 1.0 g (1.7mmol) of Pd(dba)₂, and 1.3 g (3.3 mmol) of P(t-Bu)₃, and 3.2 g (33.1mmol) of sodium butoxide were added thereto, and the mixture was heatedunder reflux at a temperature of 120° C. for 24 hours. Once the reactionwas completed, the mixture was condensed under reduced pressure, anddissolved in 400 ml of dichloromethane. The resultant was filteredthrough diatomite. An organic layer obtained therefrom was distilledunder reduced pressure by using magnesium sulfate, followed bypurification by liquid chromatography, thereby completing thepreparation of 6.4 g (11 mmol, yield of 99%) of Intermediate I-3-1.

LC-MS m/z=586 (M+H)⁺

3) Synthesis of Compound 3

1.5 g (2.5 mmol) of Intermediate I-3-1, 100 ml of o-xylene, and 20 ml ofbenzonitrile were added to a reactor at a temperature of 25° C. Then,1.2 g (2.5 mmol) of PtCl₂(NCPh)₂ was added thereto, and the resultantwas heated under reflux for 26 hours. Once the reaction was completed,the mixture was condensed under reduced pressure, and purified by liquidchromatography, thereby completing the preparation of 0.7 g (0.8 mmol,yield of 30%) of Compound 3. The obtained compound was confirmed by LCMSand ¹H NMR.

LC-MS m/z=779 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.96 (s, 2H), 7.94-7.92 (m, 4H), 7.38 (d, 2H),7.10 (s, 2H), 7.03 (t, 2H), 6.28-6.26 (m, 2H), 2.43 (s, 3H), 1.89 (s,6H), 0.41 (s, 18H).

Synthesis Example 2 Synthesis of Compound 1

1) Synthesis of Intermediate I-1-1

Intermediate I-1-1 (yield of 76%) was synthesized in the same manner asIntermediate I-3-1 in Synthesis Example 1, except that aniline was usedinstead of 2,4,6-trimethylaniline. The obtained compound was confirmedby LC-MS.

LC-MS m/z=544 (M+H)⁺

2) Synthesis of Compound 1

Compound 1 (yield of 32%) was synthesized in the same manner as Compound3 in Synthesis Example 1, except that Intermediate I-1-1 was usedinstead of Intermediate I-3-1. The obtained compound was confirmed byLCMS and ¹H NMR.

LC-MS m/z=737 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.92 (s, 2H), 7.90-7.86 (m, 4H), 7.42 (d, 2H),7.31-7.22 (m, 4H), 7.18-7.09 (m, 3H), 6.25-6.23 (m, 2H), 0.44 (s, 18H).

Synthesis Example 3 Synthesis of Compound 2

1) Synthesis of Intermediate I-2-3

10.6 g (42.2 mmol) of 2,5-dibromo-3-methylpyridine was dissolved in 200ml of diethyl ether. Then, at a temperature of −78° C., 27.0 ml ofn-BuLi (1.6 M solution in hexane) was slowly added thereto and theresultant was stirred for about 2 hours. Thereafter, 6.5 ml (50.6 mmol)of chlorotrimethylsilane was slowly added thereto, and stirred at atemperature of −78° C. for 1 hour, and at room temperature for 16 hours.Once the reaction was completed, an extraction process was performedthereon by using 200 ml of ethyl acetate and 300 ml of distilled water,and an organic layer was dried by using magnesium sulfate and distilledunder reduced pressure. The resultant obtained therefrom was purified bycolumn chromatography, thereby completing the preparation of about 8.7 g(35.9 mmol, yield of 85%) of Intermediate I-2-3. The obtained compoundwas confirmed by LC-MS.

LC-MS m/z=244 (M+H)⁺

2) Synthesis of Intermediate I-2-2

Intermediate I-2-2 (yield of 80%) was synthesized in the same manner asIntermediate I-3-2 in Synthesis Example 1, except that IntermediateI-2-3 was used instead of 2-bromo-5-(trimethylsilyl)pyridine. Theobtained compound was confirmed by LC-MS.

LC-MS m/z=320 (M+H)⁺

3) Synthesis of Intermediate I-2-1

Intermediate I-2-1 (yield of 70%) was synthesized in the same manner asIntermediate I-3-1 in Synthesis Example 1, except that IntermediateI-2-2 was used instead of Intermediate I-3-2. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=320 (M+H)⁺

4) Synthesis of Compound 2

Compound 2 (yield of 45%) was synthesized in the same manner as Compound3 in Synthesis Example 1, except that Intermediate I-2-1 was usedinstead of Intermediate I-3-1. The obtained compound was confirmed byLCMS and ¹H NMR.

LC-MS m/z=807 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.88 (s, 2H), 7.86-7.82 (m, 4H), 7.47-7.41 (m,2H), 7.16-7.11 (m, 2H), 6.78 (br s, 2H), 2.36 (s, 6H), 2.22 (s, 3H),2.09 (s, 6H).

Synthesis Example 4 Synthesis of Compound 4

1) Synthesis of Intermediate I-4-3

5.0 g (20.5 mmol) of Intermediate I-2-3 was dissolved in 300 ml oftetrahydrofuran. Then, at a temperature of −78° C., 18.0 ml of lithiumdiisopropylamide (LDA) (2.0 M solution in THF) was slowly added theretoand stirred for about 1 hour. Thereafter, the resultant was stirred atroom temperature for about 2 hours, and then, cooled to a temperature of−78° C. 2-bromopropane 3.8 ml (41.0 mmol) was slowly added thereto, andstirred at a temperature of −78° C. for 1 hour, and at room temperaturefor about 18 hours. Once the reaction was completed, an extractionprocess was performed thereon by using 200 ml of ethyl acetate and 300ml of distilled water, and an organic layer was dried by using magnesiumsulfate and distilled under reduced pressure. The resultant obtainedtherefrom was purified by column chromatography to obtain about 2.9 g(10.4 mmol, yield of 50%) of Intermediate I-4-3. The obtained compoundwas confirmed by LC-MS.

LC-MS m/z=286 (M+H)⁺

2) Synthesis of Intermediate I-4-2

Intermediate I-4-2 (yield of 65%) was synthesized in the same manner asIntermediate I-3-2 in Synthesis Example 1, except that IntermediateI-4-3 was used instead of 2-bromo-5-(trimethylsilyl)pyridine. Theobtained compound was confirmed by LC-MS.

LC-MS m/z=362 (M+H)⁺

3) Synthesis of Intermediate I-4-1

Intermediate I-4-1 (yield of 67%) was synthesized in the same manner asIntermediate I-3-1 in Synthesis Example 1, except that IntermediateI-4-2 was used instead of Intermediate I-3-2. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=698 (M+H)⁺

4) Synthesis of Compound 4

Compound 4 (yield of 28%) was synthesized in the same manner as Compound3 in Synthesis Example 1, except that Intermediate I-4-1 was usedinstead of Intermediate I-3-1. The obtained compound was confirmed byLCMS and ¹H NMR.

LC-MS m/z=807 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.91 (s, 2H), 7.88-7.84 (m, 4H), 7.50-7.45 (m,2H), 7.27-7.22 (m, 2H), 6.74 (br s, 2H), 3.15-3.11 (m, 4H), 2.28 (s,3H), 2.11 (s, 6H), 1.88-1.85 (m, 2H), 0.91 (d, 12H).

Synthesis Example 5 Synthesis of Compound 5

1) Synthesis of Intermediate I-5-3

Intermediate I-5-3 (yield of 60%) was synthesized in the same manner asIntermediate I-2-3 in Synthesis Example 3, except thatchlorotriethylsilane was used instead of chlorotrimethylsilane and2,5-dibromopyridine was used instead of 2,5-dibromo-3-methylpyridine.The obtained compound was confirmed by LC-MS.

LC-MS m/z=272 (M+H)⁺

2) Synthesis of Intermediate I-1-2

Intermediate I-36-2 (yield of 80%) was synthesized in the same manner asIntermediate I-2-2 in Synthesis Example 3, except that IntermediateI-36-3 was used instead of Intermediate I-2-3. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=348 (M+H)⁺

3) Synthesis of Intermediate I-5-1

Intermediate I-5-1 (yield of 57%) was synthesized in the same manner asIntermediate I-2-1 in Synthesis Example 3, except that IntermediateI-5-2 was used instead of Intermediate I-2-2. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=628 (M+H)⁺

4) Synthesis of Compound 5

Compound 5 (yield of 35%) was synthesized in the same manner as Compound3 in Synthesis Example 1, except that Intermediate I-5-1 was usedinstead of Intermediate I-3-1. The obtained compound was confirmed byLCMS and ¹H NMR.

LC-MS m/z=821 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) 8.98 (s, 2H), 7.98-7.93 (m, 4H), 7.36 (d, 2H),7.12 (s, 2H), 7.08-7.04 (m, 2H), 6.25-6.23 (m, 2H), 2.33 (s, 3H), 1.93(s, 6H), 1.01-0.94 (m, 18H), 0.76 (br s, 12H).

Synthesis Example 6 Synthesis of Compound 6

1) Synthesis of Intermediate I-6-3

Intermediate I-6-3 (yield of 75%) was synthesized in the same manner asIntermediate I-5-3 in Synthesis Example 5, except thatchlorotriphenylsilane was used instead of chlorotriethylsilane. Theobtained compound was confirmed by LC-MS.

LC-MS m/z=416 (M+H)⁺

2) Synthesis of Intermediate I-6-2

Intermediate I-6-2 (yield of 73%) was synthesized in the same manner asIntermediate I-5-2 in Synthesis Example 5, except that IntermediateI-6-3 was used instead of Intermediate I-5-3. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=492 (M+H)⁺

3) Synthesis of Intermediate I-6-1

Intermediate I-6-1 (yield of 60%) was synthesized in the same manner asIntermediate I-5-1 in Synthesis Example 5, except that IntermediateI-6-2 was used instead of Intermediate I-5-2, and 2,5-dimethylanilinewas used instead of 2,4,6-trimethylaniline. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=944 (M+H)⁺

4) Synthesis of Compound 6

Compound 6 (yield of 30%) was synthesized in the same manner as Compound3 in Synthesis Example 1, except that Intermediate I-6-1 was usedinstead of Intermediate I-3-1. The obtained compound was confirmed byLCMS and ¹H NMR.

LC-MS m/z=1137 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) 8.85 (s, 2H), 7.95-7.91 (m, 2H), 7.88-7.73 (m,4H), 7.58-7.22 (m, 32H), 7.14 (s, 2H), 7.04 (s, 1H), 2.31 (s, 6H).

Synthesis Example 7 Synthesis of Compound 7

1) Synthesis of Intermediate I-7-1

Intermediate I-7-1 (yield of 85%) was synthesized in the same manner asIntermediate I-3-1 in Synthesis Example 1, except that 1-naphthylaminewas used instead of 2,4,6-trimethylaniline. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=594 (M+H)⁺

2) Synthesis of Compound 7

Compound 7 (yield of 40%) was synthesized in the same manner as Compound3 in Synthesis Example 1, except that Intermediate I-7-1 was usedinstead of Intermediate I-3-1. The obtained compound was confirmed byLCMS and ¹H NMR.

LC-MS m/z=787 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.82 (s, 2H), 8.27-8.19 (m, 2H), 7.85-7.79 (m,4H), 7.72-7.45 (m, 8H), 6.98-6.94 (m, 2H), 0.38 (s, 18H).

Synthesis Example 8 Synthesis of Compound 8

1) Synthesis of Intermediate I-8-1

Intermediate I-8-1 (yield of 70%) was synthesized in the same manner asIntermediate I-3-1 in Synthesis Example 1, except that 3-aminobiphenylwas used instead of 2,4,6-trimethylaniline. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=620 (M+H)⁺

2) Synthesis of Compound 8

Compound 8 (yield of 25%) was synthesized in the same manner as Compound3 in Synthesis Example 1, except that Intermediate I-8-1 was usedinstead of Intermediate I-3-1. The obtained compound was confirmed byLCMS and ¹H NMR.

LC-MS m/z=813 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.78 (s, 2H), 7.82-7.65 (m, 8H), 7.55-7.41 (m,6H), 7.28-7.22 (m, 3H), 7.17-7.12 (m, 2H), 0.36 (s, 18H).

Synthesis Example 9 Synthesis of Compound 9

1) Synthesis of Intermediate I-9-2

Intermediate I-9-2 (yield of 75%) was synthesized in the same manner asIntermediate I-3-2 in Synthesis Example 1, except that3-bromo-5-methylphenylboronic acid was used instead of3-bromophenylboronic acid. The obtained compound was confirmed by LC-MS.

LC-MS m/z=320 (M+H)⁺

2) Synthesis of Intermediate I-9-1

Intermediate I-9-1 (yield of 53%) was synthesized in the same manner asIntermediate I-3-1 in Synthesis Example 1, except that IntermediateI-9-2 was used instead of Intermediate I-3-2. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=614 (M+H)⁺

3) Synthesis of Compound 9

Compound 9 (yield of 14%) was synthesized in the same manner as Compound3 in Synthesis Example 1, except that Intermediate I-9-1 was usedinstead of Intermediate I-3-1. The obtained compound was confirmed byLCMS and ¹H NMR.

LC-MS m/z=807 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.85 (s, 2H), 7.86-7.60 (m, 4H), 7.51 (br s,2), 7.38 (br s, 2H), 6.82 (s, 2H), 2.28 (s, 6H), 2.21 (s, 3H), 2.09 (s,6H), 0.35 (s, 18H).

Synthesis Example 10 Synthesis of Compound 10

1) Synthesis of Intermediate I-10-3

Intermediate I-10-3 (yield of 60%) was synthesized in the same manner asIntermediate I-2-3 in Synthesis Example 3, except that2,4-dibromopyridine was used instead of 2,5-dibromo-3-methylpyridine.The obtained compound was confirmed by LC-MS.

LC-MS m/z=230 (M+H)⁺

2) Synthesis of Intermediate I-10-2

Intermediate I-10-2 (yield of 70%) was synthesized in the same manner asIntermediate I-9-2 in Synthesis Example 9, except that IntermediateI-10-3 was used instead of Intermediate I-2-3. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=306 (M+H)⁺

3) Synthesis of Intermediate I-10-1

Intermediate I-10-1 (yield of 55%) was synthesized in the same manner asIntermediate I-9-1 in Synthesis Example 9, except that IntermediateI-10-2 was used instead of Intermediate I-9-2. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=586 (M+H)⁺

4) Synthesis of Compound 10

Compound 10 (yield of 12%) was synthesized in the same manner asCompound 3 in Synthesis Example 1, except that Intermediate I-10-1 wasused instead of Intermediate I-3-1. The obtained compound was confirmedby LCMS and ¹H NMR.

LC-MS m/z=779 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.52 (d, 2H), 7.84 (d, 2H), 7.75 (d, 2H),7.53-7.50 (m, 2), 7.28-7.20 (m, 4H), 6.84 (br s, 2H), 2.23 (s, 3H), 2.11(s, 6H), 0.33 (s, 18H).

Synthesis Example 11 Synthesis of Compound 11

1) Synthesis of Intermediate I-11-3

Intermediate I-11-3 (yield of 85%) was synthesized in the same manner asIntermediate I-6-3 in Synthesis Example 6, except thatchloro(dimethyl)phenylsilane was used instead of chlorotriphenylsilane.The obtained compound was confirmed by LC-MS.

LC-MS m/z=292 (M+H)⁺

2) Synthesis of Intermediate I-11-2

Intermediate I-11-2 (yield of 75%) was synthesized in the same manner asIntermediate I-6-2 in Synthesis Example 6, except that IntermediateI-11-3 was used instead of Intermediate I-6-3. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=368 (M+H)⁺

3) Synthesis of Intermediate I-11-1

Intermediate I-11-1 (yield of 55%) was synthesized in the same manner asIntermediate I-6-1 in Synthesis Example 6, except that IntermediateI-11-2 was used instead of Intermediate I-6-2. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=668 (M+H)⁺

4) Synthesis of Compound 11

Compound 11 (yield of 33%) was synthesized in the same manner asCompound 6 in Synthesis Example 6, except that Intermediate I-11-1 wasused instead of Intermediate I-6-1. The obtained compound was confirmedby LCMS and ¹H NMR.

LC-MS m/z=861 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.89 (d, 2H), 7.86-7.84 (m, 2H), 7.80-7.71 (m,2H), 7.55-7.51 (m, 2), 7.36-7.20 (m, 14H), 7.12-7.05 (m, 3H), 0.71 (s,12H).

Synthesis Example 12 Synthesis of Compound 12

1) Synthesis of Intermediate I-12-2

Intermediate I-12-2 was synthesized in the same manner as IntermediateI-11-3 and Intermediate I-11-2 in Synthesis Example 11, except thatchloro(methyl)diphenylsilane was used instead ofchloro(dimethyl)phenylsilane. The obtained compound was confirmed byLC-MS.

LC-MS m/z=430 (M+H)⁺

2) Synthesis of Intermediate I-12-1

Intermediate I-12-1 (yield of 62%) was synthesized in the same manner asIntermediate I-11-1 in Synthesis Example 11, except that IntermediateI-12-2 was used instead of Intermediate I-11-2. The obtained compoundwas confirmed by LC-MS.

LC-MS m/z=792 (M+H)⁺

3) Synthesis of Compound 12

Compound 12 (yield of 20%) was synthesized in the same manner asCompound 11 in Synthesis Example 11, except that Intermediate I-12-1 wasused instead of Intermediate I-11-1. The obtained compound was confirmedby LCMS and ¹H NMR.

LC-MS m/z=985 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.82 (br s, 2H), 8.01-7.98 (m, 2H), 7.82-7.76(m, 4H), 7.61-7.37 (m, 22H), 7.28-7.24 (m, 4H), 7.11-7.06 (m, 3H), 0.68(s, 6H).

Synthesis Example 13 Synthesis of Compound 13

1) Synthesis of Intermediate I-13-3

Intermediate I-13-3 (yield of 85%) was synthesized in the same manner asIntermediate I-10-3 in Synthesis Example 10, except thatchlorotriethylgermane was used instead of chlorotrimethylsilane. Theobtained compound was confirmed by LC-MS.

LC-MS m/z=318 (M+H)⁺

2) Synthesis of Intermediate I-13-2

Intermediate I-13-2 (yield of 70%) was synthesized in the same manner asIntermediate I-10-2 in Synthesis Example 10, except that IntermediateI-13-3 was used instead of Intermediate I-10-3. The obtained compoundwas confirmed by LC-MS.

LC-MS m/z=394 (M+H)⁺

3) Synthesis of Intermediate I-13-1

Intermediate I-13-1 (yield of 55%) was synthesized in the same manner asIntermediate I-10-1 in Synthesis Example 10, except that IntermediateI-13-2 was used instead of Intermediate I-10-2. The obtained compoundwas confirmed by LC-MS.

LC-MS m/z=762 (M+H)⁺

4) Synthesis of Compound 13

Compound 13 (yield of 10%) was synthesized in the same manner asCompound 3 in Synthesis Example 1, except that Intermediate I-13-1 wasused instead of Intermediate I-3-1. The obtained compound was confirmedby LCMS and ¹H NMR.

LC-MS m/z=955 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.64 (d, 2H), 7.88 (d, 2H), 7.82-7.79 (m, 2H),7.52 (s, 2H), 7.28-7.22 (m, 2H), 6.91 (d, 2H), 6.96 (br s, 2H), 2.26 (s,3H), 2.08 (s, 6H), 1.04 (q, 12H), 0.90 (t, 18H).

Synthesis Example 14 Synthesis of Compound 14

1) Synthesis of Intermediate I-14-1

Intermediate I-14-1 was synthesized in the same manner as IntermediatesI-13-3, I-13-2, and I-13-1 in Synthesis Example 13, except thatchlorotrimethylgermane was used instead of chlorotriethylgermane. Theobtained compound was confirmed by LC-MS.

LC-MS m/z=678 (M+H)⁺

2) Synthesis of Compound 14

Compound 14 (yield of 15%) was synthesized in the same manner asCompound 13 in Synthesis Example 13, except that Intermediate I-14-1 wasused instead of Intermediate I-13-1. The obtained compound was confirmedby LCMS and ¹H NMR.

LC-MS m/z=871 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.57 (d, 2H), 7.86 (d, 2H), 7.80-7.76 (m, 2H),7.51 (s, 2H), 7.25 (br s, 2H), 6.88 (br s, 2H), 6.80 (s, 2H), 2.23 (s,3H), 2.11 (s, 6H), 0.83 (t, 18H).

Synthesis Example 15 Synthesis of Compound 15

1) Synthesis of Intermediate I-15-1

Intermediate I-15-1 was synthesized in the same manner as IntermediatesI-5-3, I-5-2, and I-5-1 in Synthesis Example 5, except thatchlorotrimethylgermane was used instead of chlorotriethylsilane. Theobtained compound was confirmed by LC-MS.

LC-MS m/z=678 (M+H)⁺

2) Synthesis of Compound 15

Compound 15 (yield of 25%) was synthesized in the same manner asCompound 5 in Synthesis Example 5, except that Intermediate I-15-1 wasused instead of Intermediate I-5-1. The obtained compound was confirmedby LCMS and ¹H NMR.

LC-MS m/z=871 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.47 (br s, 2H), 7.84-7.78 (m, 4H), 7.61 (brs, 2H), 7.36-7.21 (m, 4H), 6.76 (s, 2H), 2.21 (s, 3H), 2.09 (s, 6H),0.79 (s, 18H).

Synthesis Example 16 Synthesis of Compound 16

1) Synthesis of Intermediate I-16-3

Intermediate I-16-3 (yield of 55%) was synthesized in the same manner asIntermediate I-5-3 in Synthesis Example 5, except that5-bromo-2-chloropyrimidine was used instead of 2,5-dibromopyridine. Theobtained compound was confirmed by LC-MS.

LC-MS m/z=187 (M+H)⁺

2) Synthesis of Intermediate I-16-2

Intermediate I-11-1 (yield of 55%) was synthesized in the same manner asIntermediate I-6-1 in Synthesis Example 6, except that IntermediateI-11-2 was used instead of Intermediate I-6-2. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=307 (M+H)⁺

3) Synthesis of Intermediate I-16-1

Intermediate I-16-1 (yield of 80%) was synthesized in the same manner asIntermediate I-5-1 in Synthesis Example 5, except that IntermediateI-16-2 was used instead of Intermediate I-5-2. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=588 (M+H)⁺

3) Synthesis of Compound 16

5.0 g (8.5 mmol) of Intermediate I-16-1 and 300 ml of an acetic acidwere added to a reactor at a temperature of 25° C. Then, 3.5 g (8.5mmol) of K₂PtCl₄ was added thereto, and the mixture was heated underreflux for 48 hours. Once the reaction was completed, the mixture wascondensed under reduced pressure, and re-crystallized by usingdichloromethane and methanol to complete the preparation of 0.5 g (0.8mmol, yield of 8%) of Compound 16. The obtained compound was confirmedby LC-MS.

LC-MS m/z=781 (M+H)⁺

Synthesis Example 17 Synthesis of Compound 17

1) Synthesis of Intermediate I-17-1

30.0 g (51.0 mmol) of P-SM (a compound prepared in response to an order,Medigen, Inc., www.medi-gen.net), 600 ml of tetrahydrofuran, and 300 mlof distilled water were added to a reactor. 28.1 g (122.4 mmol) of2-bromo-5-(trimethylsilyl)pyridine, 5.9 g (5.1 mmol) of Pd(PPh₃)₄, and21.1 g (153.0 mmol) of K₂CO₃ were added thereto, and the mixture washeated under reflux at a temperature of 80° C. for 18 hours. Once thereaction was completed, an extraction process was performed thereon byusing 400 ml of ethyl acetate and 100 ml of distilled water. An organiclayer obtained therefrom was dried by using magnesium sulfate anddistilled under reduced pressure. The resultant was purified by liquidchromatography to complete the preparation of 24.0 g (38 mmol, yield of75%) of Intermediate I-17-1.

LC-MS m/z=635 (M+H)⁺

2) Synthesis of Compound 17

Compound 17 (yield of 35%) was synthesized in the same manner asCompound 3 in Synthesis Example 1, except that Intermediate I-17-1 wasused instead of Intermediate I-3-1. The obtained compound was confirmedby LCMS and ¹H NMR.

LC-MS m/z=828 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.81 (br s, 2H), 8.37 (br s, 2H), 7.85 (br s,2H), 7.72-7.58 (m, 4H), 7.46-7.44 (m, 2H), 7.42-7.32 (m, 10H), 0.42 (s,18H).

Synthesis Example 18 Synthesis of Compound 18

1) Synthesis of Intermediate I-18-1

Intermediate I-18-1 (yield of 60%) was synthesized in the same manner asIntermediate I-17-1 in Synthesis Example 17, except that IntermediateI-2-3 was used instead of 2-bromo-5-(trimethylsilyl)pyridine. Theobtained compound was confirmed by LC-MS.

LC-MS m/z=663 (M+H)⁺

2) Synthesis of Compound 18

Compound 18 (yield of 20%) was synthesized in the same manner asCompound 17 in Synthesis Example 17, except that Intermediate I-18-1 wasused instead of Intermediate I-17-1. The obtained compound was confirmedby LCMS and ¹H NMR.

LC-MS m/z=856 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.79 (br s, 2H), 8.26 (br s, 2H), 7.88 (s,2H), 7.64-7.56 (m, 4H), 7.46-7.38 (m, 10H), 2.36 (s, 6H), 0.77 (s, 18H).

Synthesis Example 19 Synthesis of Compound 20

1) Synthesis of Intermediate I-20-1

Intermediate I-20-1 (yield of 53%) was synthesized in the same manner asIntermediate I-18-1 in Example 18, except that1-bromo-4-(trimethylsilyl)isoquinoline (a compound prepared in responseto an order, HANCHEM CO., LTD., www.hanchem.co.kr) was used instead ofIntermediate I-2-3. The obtained compound was confirmed by LC-MS.

LC-MS m/z=735 (M+H)⁺

2) Synthesis of Compound 20

Compound 20 (yield of 10%) was synthesized in the same manner asCompound 17 in Synthesis Example 17, except that Intermediate I-20-1 wasused instead of Intermediate I-17-1. The obtained compound was confirmedby LC-MS.

LC-MS m/z=927 (M+H)⁺

Synthesis Example 20 Synthesis of Compound 21

1) Synthesis of Intermediate I-21-1

Intermediate I-21-1 (yield of 50%) was synthesized in the same manner asIntermediate I-18-1 in Example 18, except that1-bromo-7-(trimethylsilyl)isoquinoline (a compound prepared in responseto an order, HANCHEM CO., LTD., www.hanchem.co.kr) was used instead ofIntermediate I-2-3. The obtained compound was confirmed by LC-MS.

LC-MS m/z=735 (M+H)⁺

2) Synthesis of Compound 21

Compound 21 (yield of 7%) was synthesized in the same manner as Compound17 in Synthesis Example 17, except that Intermediate I-20-1 was usedinstead of Intermediate I-17-1. The obtained compound was confirmed byLC-MS.

LC-MS m/z=927 (M+H)⁺

Synthesis Example 21 Synthesis of Compound 22

1) Synthesis of Intermediate I-22-1

Intermediate I-22-1 (yield of 62%) was synthesized in the same manner asIntermediate I-17-1 in Example 17, except that P-SM2 (a compoundprepared in response to an order, Medigen, Inc., www.medi-gen.net) wasused instead of P-SM, and Intermediate I-4-3 was used instead ofIntermediate I-2-3. The obtained compound was confirmed by LC-MS.

LC-MS m/z=581 (M+H)⁺

2) Synthesis of Compound 22

Compound 22 (yield of 22%) was synthesized in the same manner asCompound 17 in Synthesis Example 17, except that Intermediate I-22-1 wasused instead of Intermediate I-17-1. The obtained compound was confirmedby and ¹H NMR.

LC-MS m/z=774 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.86 (br s, 2H), 7.95 (d, 2H), 7.83 (br s,2H), 7.52-7.48 (m, 2H), 7.33-7.25 (m, 2H), 3.16 (d, 4H), 1.96-1.93 (m,2H), 1.00 (d, 12H), 0.41 (s, 18H).

Synthesis Example 22 Synthesis of Compound 23

1) Synthesis of Intermediate I-23-1

Intermediate I-23-1 (yield of 76%) was synthesized in the same manner asIntermediate I-18-1 in Synthesis Example 18, except that IntermediateI-15-3 was used instead of Intermediate I-2-3. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=727 (M+H)⁺

2) Synthesis of Compound 23

Compound 23 (yield of 21%) was synthesized in the same manner asCompound 17 in Synthesis Example 17, except that Intermediate I-23-1 wasused instead of Intermediate I-17-1. The obtained compound was confirmedby LCMS and ¹H NMR.

LC-MS m/z=920 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.42 (s, 2H), 8.15 (br s, 2H), 7.78 (br s,2H), 7.68-7.61 (m, 2H), 7.58-7.54 (m, 2H), 7.46-7.32 (m, 10H), 0.72 (s,18H).

Synthesis Example 23 Synthesis of Compound 24

3) Synthesis of Intermediate I-24-1

Intermediate I-13-1 (yield of 55%) was synthesized in the same manner asIntermediate I-10-1 in Synthesis Example 10, except that IntermediateI-13-2 was used instead of Intermediate I-10-2. The obtained compoundwas confirmed by LC-MS.

LC-MS m/z=593 (M+H)⁺

2) Synthesis of Compound 24

Compound 24 (yield of 25%) was synthesized in the same manner asCompound 22 in Synthesis Example 21, except that Intermediate I-24-1 wasused instead of Intermediate I-22-1. The obtained compound was confirmedby LCMS and ¹H NMR.

LC-MS m/z=786 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.82 (s, 2H), 7.93-7.77 (m, 4H), 7.69-7.64 (m,2H), 7.43-7.34 (m, 2H), 7.31-7.21 (m, 10H), 7.15-7.10 (m, 2H), 0.67 (s,12H).

Synthesis Example 24 Synthesis of Compound 25

1) Synthesis of Intermediate I-25-1

Intermediate I-25-1 (yield of 83%) was synthesized in the same manner asIntermediate I-23-1 in Synthesis Example 22, except that P-SM3 (acompound prepared in response to an order, HANCHEM CO., LTD.,www.hanchem.co.kr) was used instead of P-SM. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=709 (M+H)⁺

2) Synthesis of Compound 25

Compound 25 (yield of 36%) was synthesized in the same manner asCompound 23 in Synthesis Example 22, except that Intermediate I-25-1 wasused instead of Intermediate I-23-1. The obtained compound was confirmedby LCMS and ¹H NMR.

LC-MS m/z=902 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.41 (s, 2H), 8.11 (d, 2H), 8.00-7.97 (m, 2H),7.85-7.82 (m, 2H), 7.53-7.38 (m, 4H), 7.37-7.32 (m, 4H), 7.28-7.22 (m,2H), 0.72 (s, 18H).

Synthesis Example 25 Synthesis of Compound 26

1) Synthesis of Intermediate I-26-1

Intermediate I-26-1 (yield of 75%) was synthesized in the same manner asIntermediate I-25-1 in Synthesis Example 24, except that2-bromo-5-(trimethylsilyl)pyridine was used instead of IntermediateI-15-3. The obtained compound was confirmed by LC-MS.

LC-MS m/z=617 (M+H)⁺

2) Synthesis of Compound 26

Compound 26 (yield of 30%) was synthesized in the same manner asCompound 25 in Synthesis Example 24, except that Intermediate I-26-1 wasused instead of Intermediate I-25-1. The obtained compound was confirmedby LCMS and ¹H NMR.

LC-MS m/z=810 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.75 (br s, 2H), 8.08 (d, 2H), 7.94-7.90 (m,2H), 7.84 (d, 2H), 7.70-7.64 (m, 2H), 7.55-7.51 (m, 4H), 7.38-7.35 (m,2H), 7.28-7.24 (m, 4H), 0.42 (s, 18H).

Synthesis Example 26 Synthesis of Compound 27

1) Synthesis of Intermediate I-27-1

Intermediate I-27-1 (yield of 52%) was synthesized in the same manner asIntermediate I-25-1 in Synthesis Example 24, except that1-bromo-4-(trimethylsilyl)isoquinoline (a compound prepared in responseto an order, HANCHEM CO., LTD., www.hanchem.co.kr) was used instead ofIntermediate I-15-3. The obtained compound was confirmed by LC-MS.

LC-MS m/z=717 (M+H)⁺

2) Synthesis of Compound 27

Compound 27 (yield of 8%) was synthesized in the same manner as Compound25 in Synthesis Example 24, except that Intermediate I-27-1 was usedinstead of Intermediate I-25-1. The obtained compound was confirmed byLC-MS.

LC-MS m/z=909 (M+H)⁺

Synthesis Example 27 Synthesis of Compound 28

1) Synthesis of Intermediate I-28-3

Intermediate I-28-3 (yield of 75%) was synthesized in the same manner asIntermediate I-5-3 in Synthesis Example 5, except that2,5-dibromo-4-phenylpyridine was used instead of 2,5-dibromopyridine.The obtained compound was confirmed by LC-MS.

LC-MS m/z=306 (M+H)⁺

3) Synthesis of Intermediate I-28-1

Intermediate I-13-1 (yield of 55%) was synthesized in the same manner asIntermediate I-10-1 in Synthesis Example 10, except that IntermediateI-13-2 was used instead of Intermediate I-10-2. The obtained compoundwas confirmed by LC-MS.

LC-MS m/z=382 (M+H)⁺

3) Synthesis of Intermediate I-28-1

Intermediate I-28-1 (yield of 60%) was synthesized in the same manner asIntermediate I-5-1 in Synthesis Example 5, except that IntermediateI-28-2 was used instead of Intermediate I-5-2, and 2-aminobiphenyl wasused instead of 2,4,6-trimethylaniline. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=772 (M+H)⁺

3) Synthesis of Compound 28

2.8 g (3.6 mmol) of Intermediate I-28-1 and 100 ml of benzonitrile wereadded to a reactor at a temperature of 25° C. Then, 1.7 g (3.6 mmol) ofPtCl₂(NCPh)₂ was added thereto, and the resultant was mixed for 16 hoursfor 130° C. Once the reaction was completed, the mixture wasconcentrated under reduced pressure, and purified by columnchromatography, thereby completing the preparation of 0.9 g (0.9 mmol,yield of 26%) of Compound 28. The obtained compound was confirmed byLC-MS.

LC-MS m/z=965 (M+H)⁺

Synthesis Example 28 Synthesis of Compound 29

1) Synthesis of Intermediate I-29-2

Intermediate I-29-2 (yield of 70%) was synthesized in the same manner asIntermediate I-3-2 in Synthesis Example 1, except that(5-bromo-[1,1′-biphenyl]-3-yl)boronic acid was used instead of3-bromophenylboronic acid. The obtained compound was confirmed by LC-MS.

LC-MS m/z=382 (M+H)⁺

2) Synthesis of Intermediate I-29-1

Intermediate I-29-1 (yield of 75%) was synthesized in the same manner asIntermediate I-3-1 in Synthesis Example 1, except that IntermediateI-29-2 was used instead of Intermediate I-3-2, and 2-aminobiphenyl wasused instead of 2,4,6-trimethylaniline. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=772 (M+H)⁺

3) Synthesis of Compound 29

Compound 29 (yield of 25%) was synthesized in the same manner asCompound 28 in Synthesis Example 27, except that Intermediate I-29-1 wasused instead of Intermediate I-28-1. The obtained compound was confirmedby LCMS and ¹H NMR.

LC-MS m/z=965 (M+H)⁺

¹H NMR (300 MHz, CD₂Cl₂) δ=9.05 (s, 2H), 8.07 (s, 4H), 7.68-7.65 (m,1H), 7.64-7.62 (m, 4H), 7.51-7.48 (m, 4H), 7.42-7.31 (m, 9H), 7.13-7.11(m, 3H), 6.65 (s, 2H), 0.48 (s, 18H).

Synthesis Example 29 Synthesis of Compound 30

1) Synthesis of Intermediate I-30-1

Intermediate I-30-1 (yield of 70%) was synthesized in the same manner asIntermediate I-29-1 in Synthesis Example 28, except that4-(trimethylsilyl)naphthalene-1-amine was used instead of2-aminobiphenyl. The obtained compound was confirmed by LC-MS.

LC-MS m/z=818 (M+H)⁺

2) Synthesis of Compound 30

Compound 30 (yield of 17%) was synthesized in the same manner asCompound 28 in Synthesis Example 27, except that Intermediate I-30-1 wasused instead of Intermediate I-28-1. The obtained compound was confirmedby LC-MS.

LC-MS m/z=1011 (M+H)⁺

Synthesis Example 30 Synthesis of Compound 31

1) Synthesis of Intermediate I-31-1

Intermediate I-31-1 (yield of 75%) was synthesized in the same manner asIntermediate I-29-1 in Synthesis Example 28, except that4-isobutylnaphthalene-1-amine was used instead of 2-aminobiphenyl. Theobtained compound was confirmed by LC-MS.

LC-MS m/z=802 (M+H)⁺

2) Synthesis of Compound 31

Compound 31 (yield of 15%) was synthesized in the same manner asCompound 28 in Synthesis Example 27, except that Intermediate I-31-1 wasused instead of Intermediate I-28-1. The obtained compound was confirmedby LCMS and ¹H NMR.

LC-MS m/z=995 (M+H)⁺

¹H NMR (300 MHz, CD₂Cl₂) δ=9.04 (s, 2H), 8.52 (br s, 1H), 8.36-8.34 (m,3H), 7.75-7.69 (m, 8H), 7.49-7.41 (m, 8H), 7.38-7.36 (m, 2H), 7.29 (brs, 1H), 6.84 (s, 1H), 2.86 (d, 2H), 1.86 (q, 1H), 0.91 (d, 6H).

Synthesis Example 31 Synthesis of Compound 32

1) Synthesis of Intermediate I-32-1

Intermediate I-32-1 (yield of 50%) was synthesized in the same manner asIntermediate I-29-1 in Synthesis Example 28, except that2-(2-bromodibenzo[b,d]furan-4-yl)-5-(trimethylsilyl)pyridine was usedinstead of Intermediate I-29-2, and [4,4′-bipyridine]-3-amine was usedinstead of 2-aminobiphenyl. The obtained compound was confirmed byLC-MS.

LC-MS m/z=802 (M+H)⁺

2) Synthesis of Compound 32

Compound 31 (yield of 15%) was synthesized in the same manner asCompound 28 in Synthesis Example 27, except that Intermediate I-31-1 wasused instead of Intermediate I-28-1. The obtained compound was confirmedby LCMS and ¹H NMR.

LC-MS m/z=995 (M+H)⁺

¹H NMR (300 MHz, CD₂Cl₂) δ=9.18 (s, 2H), 8.92 (d, 2H), 8.65 (d, 1H),8.42 (s, 2H), 8.23 (s, 1H), 8.01-7.97 (m, 3H), 7.80-7.77 (m, 3H), 7.61(d, 2H), 7.54 (d, 2H), 7.39-7.31 (m, 4H).

Synthesis Example 32 Synthesis of Compound 33

1) Synthesis of Intermediate I-33-4

9.1 g (25.3 mmol) of 1,3-dibromo-5-iodobenzene, 200 ml of 1,4-dioxane,and 100 ml of distilled water were added to a reactor. 5.2 g (25.3 mmol)of 2,6-diisopropylphenyl boronic acid, 1.5 g (1.3 mmol) of Pd(PPh₃)₄,and 7.8 g (45.5 mmol) of Ba(OH)₂ were added thereto, and the mixture washeated at a temperature of 80° C. for 18 hours. Once the reaction wascompleted, the mixture was condensed under reduced pressure, anddissolved in 200 ml of dichloromethane, and filtered through diatomite.An organic layer obtained therefrom was dried by using magnesiumsulfate, distilled under reduced pressure, and purified by liquidchromatography, thereby completing the preparation of 8.1 g (20.5 mmol,yield of 81%) of Intermediate I-33-4.

LC-MS m/z=394 (M+H)⁺

2) Synthesis of Intermediate I-33-3

6.0 g (15.1 mmol) of Intermediate I-33-4 was dissolved in 150 ml ofdiethyl ether. Then, at a temperature of −78° C., 6.6 ml of n-BuLi (2.5M solution in hexane) was slowly added thereto, and stirred for about 1hour. Then, tri-n-butyltin chloride was slowly added dropwise theretoand stirred for about 2 hours. Then, the resultant was slowly heated atroom temperature and stirred for about 18 hours. Once the reaction wascompleted, an extraction process was performed thereon by using 80 ml ofdistilled water and 100 ml of ethyl acetate. An organic layer obtainedtherefrom was dried by using magnesium sulfate and distilled underreduced pressure, thereby completing the preparation of IntermediateI-33-3. The obtained Intermediate I-33-3 was used for the followingreaction without any subjection to a separate purification process.

3) Synthesis of Intermediate I-33-2

11.8 g (19.5 mmol) of Intermediate I-33-3, 4.5 g (19.5 mmol) of2-bromo-5-(trimethylsilyl)pyridine were added to a reactor. Then, 150 mlof toluene was added thereto. Then, 1.0 g (1.0 mmol) of Pd(PPh₃)₄ and2.3 g (40.0 mmol) of KF were added thereto, and the mixture was heatedat a temperature of 120° C. for 12 hours. Once the reaction wascompleted, the mixture was extracted by using 100 ml of ethyl acetate,and a saturated NH₄Cl aqueous solution. An organic layer obtainedtherefrom was dried by using magnesium sulfate, and distilled underreduced pressure, and purified by liquid chromatography, therebycompleting the preparation of 6.2 g (13.3 mmol, yield of 68%) ofIntermediate I-33-2.

LC-MS m/z=466 (M+H)⁺

4) Synthesis of Intermediate I-33-1

Intermediate I-33-1 (yield of 65%) was synthesized in the same manner asIntermediate I-29-1 in Synthesis Example 28, except that IntermediateI-33-2 was used instead of Intermediate I-29-2. The obtained compoundwas confirmed by LC-MS.

LC-MS m/z=940 (M+H)⁺

5) Synthesis of Compound 33

Compound 33 (yield of 30%) was synthesized in the same manner asCompound 28 in Synthesis Example 27, except that Intermediate I-33-1 wasused instead of Intermediate I-28-1. The obtained compound was confirmedby LCMS and ¹H NMR.

LC-MS m/z=1133 (M+H)⁺

¹H NMR (300 MHz, CD₂Cl₂) δ=8.66 (s, 2H), 7.75 (d, 2H), 7.61 (br s, 2H),7.45-7.39 (m, 3H), 7.32-7.24 (m, 12H), 7.14-7.09 (m, 7H), 6.84-6.83 (m,2H), 2.68 (br s, 4H), 1.06 (d, 12H), 0.94 (d, 12H), 0.30 (s, 18H).

Synthesis Example 33 Synthesis of Compound 34

1) Synthesis of Intermediate I-34-4

Intermediate I-34-4 was synthesized in the same manner as IntermediateI-33-4 in Synthesis Example 32, except that 3,5-di-tert-butylphenylboronic acid was used instead of 2,6-diisopropylphenyl boronic acid.

2) Synthesis of Intermediate I-34-3

Intermediate I-34-3 was synthesized in the same manner as IntermediateI-33-3 in Synthesis Example 32, except that Intermediate I-34-4 was usedinstead of Intermediate I-33-4.

3) Synthesis of Intermediate I-34-2

Intermediate I-34-2 was synthesized in the same manner as IntermediateI-33-2 in Synthesis Example 32, except that Intermediate I-34-3 was usedinstead of Intermediate I-33-3.

4) Synthesis of Intermediate I-34-1

Intermediate I-34-1 was synthesized in the same manner as IntermediateI-29-1 in Synthesis Example 28, except that Intermediate I-34-2 was usedinstead of Intermediate I-29-2, and 2-aminobiphenyl was used instead of2,4,6-trimethylaniline.

5) Synthesis of Compound 34

Compound 34 (yield of 25%) was synthesized in the same manner asCompound 28 in Synthesis Example 27, except that Intermediate I-34-1 wasused instead of Intermediate I-28-1. The obtained compound was confirmedby LC-MS.

LC-MS m/z=1189 (M+H)⁺

Synthesis Example 34 Synthesis of Compound 35

1) Synthesis of Intermediate I-35-1

Intermediate I-35-1 (yield of 70%) was synthesized in the same manner asIntermediate I-8-1 in Synthesis Example 8, except thatdibenzo[b,d]furan-1-amine was used instead of 3-aminobiphenyl. Theobtained compound was confirmed by LC-MS.

LC-MS m/z=634 (M+H)⁺

2) Synthesis of Compound 35

Compound 35 (yield of 30%) was synthesized in the same manner asCompound 8 in Synthesis Example 8, except that Intermediate I-35-1 wasused instead of Intermediate I-8-1. The obtained compound was confirmedby LCMS and ¹H NMR.

LC-MS m/z=827 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.76 (br s, 2H), 7.98 (d, 1H), 7.83-7.79 (m,4H), 7.70-7.68 (m, 2H), 7.56-7.50 (m, 3H), 7.34-7.22 (m, 6H), 6.98 (brs, 1H), 0.28 (s, 18H).

Synthesis Example 35 Synthesis of Compound 36

1) Synthesis of Intermediate I-36-3

Intermediate I-36-3 (yield of 70%) was synthesized in the same manner asIntermediate I-2-3 in Synthesis Example 3, except that1-chloro-1-methylsiletane was used instead of chlorotrimethylsilane. Theobtained compound was confirmed by LC-MS.

LC-MS m/z=242 (M+H)⁺

2) Synthesis of Intermediate I-36-2

Intermediate I-36-2 (yield of 80%) was synthesized in the same manner asIntermediate I-2-2 in Synthesis Example 3, except that IntermediateI-36-3 was used instead of Intermediate I-2-3. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=318 (M+H)⁺

3) Synthesis of Intermediate I-36-1

Intermediate I-36-1 (yield of 62%) was synthesized in the same manner asIntermediate I-2-1 in Synthesis Example 3, except that IntermediateI-36-2 was used instead of Intermediate I-2-2. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=610 (M+H)⁺

4) Synthesis of Compound 36

Compound 36 (yield of 25%) was synthesized in the same manner asCompound 3 in Synthesis Example 1, except that Intermediate I-36-1 wasused instead of Intermediate I-3-1. The obtained compound was confirmedby LCMS and ¹H NMR.

LC-MS m/z=803 (M+H)⁺

Synthesis Example 36 Synthesis of Compound 37

1) Synthesis of Intermediate I-37-2

Intermediate I-37-2 (yield of 75%) was synthesized in the same manner asIntermediate I-2-2 in Synthesis Example 3, except that(3-bromo-5-(9H-carbazole-9-yl)phenyl)boronic acid was used instead ofIntermediate I-2-3. The obtained compound was confirmed by LC-MS.

LC-MS m/z=471 (M+H)⁺

2) Synthesis of Intermediate I-37-1

Intermediate I-37-1 (yield of 55%) was synthesized in the same manner asIntermediate I-2-1 in Synthesis Example 3, except that IntermediateI-37-2 was used instead of Intermediate I-2-2. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=950 (M+H)⁺

3) Synthesis of Compound 37

Compound 31 (yield of 15%) was synthesized in the same manner asCompound 28 in Synthesis Example 27, except that Intermediate I-31-1 wasused instead of Intermediate I-28-1. The obtained compound was confirmedby LCMS and ¹H NMR.

LC-MS m/z=1143 (M+H)⁺

Example 1

An ITO/Ag/ITO (70 Å/1,000 Å/70 Å) substrate (anode) was cut to a size of50 mm×50 mm×0.5 mm (mm=millimeter), sonicated by using iso-propylalcohol and distilled water, each for 5 minutes, washed by exposure toultraviolet rays for 30 minutes, and then − to ozone. The resultantsubstrate was mounted on a deposition apparatus.

2-TNATA was vacuum-deposited on the substrate to form a hole injectionlayer having a thickness of 600 Å, and then,4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) wasvacuum-deposited on the hole injection layer to form a hole transportlayer having a thickness of 1,000 Å.

CBP (host) and Compound 17 (dopant) were co-deposited at a weight ratioof 91:9 on the hole transport layer to form an emission layer having athickness of 250 Å.

BCP was vacuum-deposited on the emission layer to form a hole blockinglayer having a thickness of 50 Å. Alq₃ was deposited on the holeblocking layer to form an electron transport layer having a thickness of350 Å, and LiF was deposited on the electron transport layer to form anelectron injection layer having a thickness of 10 Å.

Mg and Ag were co-deposited at a weight ratio of 90:10 on the electroninjection layer to form a cathode having a thickness of 120 Å, therebycompleting manufacture of an organic light-emitting device.

Example 2

An organic light-emitting device was manufactured in the same manner asin Example 1, except that, in forming the emission layer, Compound 24was used instead of Compound 17.

Example 3

An organic light-emitting device was manufactured in the same manner asin Example 1, except that, in forming the emission layer, Compound 25was used instead of Compound 17.

Example 4

An ITO/Ag/ITO (70 Å/1,000 Å/70 Å) substrate (anode) was cut to a size of50 mm×50 mm×0.5 mm, sonicated by using iso-propyl alcohol and distilledwater, each for 5 minutes, washed by exposure to ultraviolet rays for 30minutes, and then − to ozone. The resultant substrate was mounted on adeposition apparatus.

2-TNATA was vacuum-deposited on the substrate to form a hole injectionlayer having a thickness of 600 Å,4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) wasvacuum-deposited on the hole injection layer to form a hole transportlayer having a thickness of 1,350 Å.

CBP (host) and Compound 3 (dopant) were co-deposited at a weight ratioof 94:6 on the hole transport layer to form an emission layer having athickness of 400 Å.

BCP was vacuum-deposited on the emission layer to form a hole blockinglayer having a thickness of 50 Å. Alq₃ was deposited on the holeblocking layer to form an electron transport layer having a thickness of350 Å, and LiF was deposited on the electron transport layer to form anelectron injection layer having a thickness of 10 Å.

Mg and Ag were co-deposited at a weight ratio of 90:10 on the electroninjection layer to form a cathode having a thickness of 120 Å, therebycompleting manufacture of an organic light-emitting device.

Example 5

An organic light-emitting device was manufactured in the same manner asin Example 4, except that, in forming the emission layer, Compound 7 wasused instead of Compound 3.

Example 6

An organic light-emitting device was manufactured in the same manner asin Example 4, except that, in forming the emission layer, Compound 11was used instead of Compound 3.

Example 7

An organic light-emitting device was manufactured in the same manner asin Example 4, except that, in forming the emission layer, Compound 13was used instead of Compound 3.

Example 8

An organic light-emitting device was manufactured in the same manner asin Example 4, except that, in forming the emission layer, Compound 28was used instead of Compound 3.

Example 9

An organic light-emitting device was manufactured in the same manner asin Example 4, except that, in forming the emission layer, Compound 29was used instead of Compound 3.

Comparative Example 1

An organic light-emitting device was manufactured in the same manner asin Example 1, except that, in forming the emission layer, Compound A wasused instead of Compound 17:

Comparative Example 2

An organic light-emitting device was manufactured in the same manner asin Example 1, except that, in forming the emission layer, Compound B wasused instead of Compound 17:

Comparative Example 3

An organic light-emitting device was manufactured in the same manner asin Example 4, except that, in forming the emission layer, Compound C wasused instead of Compound 3:

Comparative Example 4

An organic light-emitting device was manufactured in the same manner asin Example 4, except that, in forming the emission layer, Compound D wasused instead of Compound 3:

Comparative Example 4

An organic light-emitting device was manufactured in the same manner asin Example 4, except that, in forming the emission layer, Compound E wasused instead of Compound 3:

Evaluation Example 1 Evaluation on Characteristics of OrganicLight-Emitting Devices

The driving voltage, current density, luminance, efficiency, emissioncolor, CIE color coordinate, and lifespan (LT₉₇) of each of the organiclight-emitting devices manufactured according to Examples 1 to 9 andComparative Examples 1 to 5 were evaluated. Evaluation results are shownin Table 1. LT₉₇ refers to a lifetime, and LT₉₇ indicates a period oftime that elapses until the luminance is reduced to 97% of the initialluminance:

TABLE 1 Driving Current CIE color voltage density Luminance EfficiencyEmission coordinate LT₉₇ Dopant (V) (mA/cm²) (cd/m²) (cd/A) color (x, y)(hr) Example 1 Compound 17 5.6 10 5,540 55.4 Green 0.27, 0.72 90 Example2 Compound 24 5.6 10 5,864 58.6 Green 0.24, 0.70 95 Example 3 Compound25 5.5 10 6,296 62.9 Green 0.26, 0.71 98 Example 4 Compound 3 5.5 103,010 30.1 Red 0.66,0.34 1600 Example 5 Compound 7 5.3 10 3,227 32.3 Red0.65, 0.35 1800 Example 6 Compound 11 5.5 10 3,570 35.7 Red 0.64, 0.321200 Example 7 Compound 13 5.6 10 3,387 33.8 Red 0.63, 0.34 1000 Example8 Compound 28 5.3 10 3,608 36.1 Red 0.64, 0.34 1000 Example 9 Compound29 5.3 10 3,485 34.9 Red 0.65, 0.33 1300 Comparative Compound A 6.8 104,766 47.7 Green 0.27, 0.70 61 Example 1 Comparative Compound B 6.0 105,237 52.3 Green 0.25, 0.73 82 Example 2 Comparative Compound C 7.3 102,212 22.1 Red 0.67, 0.32 80 Example 3 Comparative Compound D 5.7 102,530 25.3 Red 0.63, 0.33 210 Example 4 Comparative Compound E 5.9 101,213 12.1 Red 0.62, 0.32 375 Example 5

Referring to Table 1, the driving voltage of each of the organiclight-emitting devices of Examples 1 to 3 is about 0.5 to 1.2 volts (V)lower than that of each of the organic light-emitting devices ofComparative Examples 1 and 2. In addition, the organic light-emittingdevices of Examples 1 to 3 have higher efficiency and a longer lifespanand better l-V-L characteristics than those of Comparative Examples 1and 2. In addition, the organic light-emitting devices of Examples 1 to3 have a higher level of luminance than the organic light-emittingdevices of Comparative Examples 1 to 2.

The organic light-emitting devices of Examples 4 to 9 have higherefficiency and longer lifespan and better l-V-L characteristics thanthose of Comparative Examples 3 to 5. In addition, the organiclight-emitting devices of Examples 4 to 9 have a higher level ofluminance and a longer lifespan than those of Comparative Examples 3 to5.

In detail, as in Example 1, when the organometallic compound representedby Formula 1 was used as a green phosphorescent dopant, compared toComparative Example 1, the driving voltage was increased by 1.2 V ormore, the efficiency was increased to 110%, and the lifespan wasincreased to 150%. In the case of Example 3, compared to ComparativeExample 2, the driving voltage was improved by 0.5 V or more, theefficiency was increased to 120%, and the lifespan was increased to120%.

As in Examples 4 to 9, when the organometallic compound represented byFormula 1 was used as a red phosphorescent dopant, compared toComparative Example 3, the driving voltage was increased by about 2.0 V,the efficiency was increased to 140%, and the lifespan was increased to1,000% or more.

The organometallic compounds according to embodiments have excellentelectric characteristics and thermal stability. Accordingly, an organiclight-emitting device including the organometallic compound may haveexcellent driving voltage, current density, efficiency, power, colorpurity, and lifespan characteristics.

While the inventive concept has been particularly shown and describedwith reference to exemplary embodiments thereof, it will be understoodby those of ordinary skill in the art that various changes in form anddetails may be made therein without departing from the spirit and scopeof the present disclosure as defined by the following claims.

What is claimed is:
 1. An organometallic compound represented by Formula1:

wherein, in Formula 1, M is selected from a Period 1 transition metal, aPeriod 2 transition metal, and a Period 3 transition metal; A₁ to A₄ areeach independently selected from a C₅-C₂₀ carbocyclic group and a C₁-C₂₀heterocyclic group; X₁ to X₄ are each independently selected from acarbon atom (C) and a nitrogen atom (N), provided that at least oneselected from X₃ and X₄ is N; B₁ to B₄ are each independently selectedfrom a single bond, O, and S; Y₁ to Y₃ are each independently selectedfrom a single bond and a divalent linking group, at least one selectedfrom Y₁ to Y₃ is a divalent linking group; Z₁ and Z₂ are eachindependently represented by one of Formulae 2-1 to 2-4:

wherein, in Formulae 2-1 to 2-4, Y₂₁ and Y₂₂ are each independentlyselected from a substituted or unsubstituted C₁-C₁₀ alkylene group and asubstituted or unsubstituted C₂-C₁₀ alkenylene group; a21 and a22 areeach independently selected from 0, 1, 2, 3, 4, and 5; R₂₁ to R₂₇ areeach independently selected from hydrogen, deuterium, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₇-C₆₀ arylalkyl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryl group, a substituted or unsubstituted C₁-C₆₀heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group;d1 and d2 are each independently selected from 0, 1, 2, 3, and 4; whend1 is 2 or more, groups Z₁ are identical to or different from eachother; when d2 is 2 or more, groups Z₂ are identical to or differentfrom each other; when X₃ is N, d1 is selected from 1, 2, 3, and 4; orwhen X₄ is N, d2 is selected from 1, 2, 3, and 4; R₁ to R₄ are eachindependently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₇-C₆₀ arylalkylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted C₁-C₆₀ heteroaryloxy group, a substitutedor unsubstituted C₁-C₆₀ heteroarylthio group, a substituted orunsubstituted C₂-C₆₀ heteroarylalkyl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —C(═O)(Q₇), and —N(Q₇)(Q₈); R₁ and R₄ or R₂ andR₃ are optionally linked to form a saturated or unsaturated ring; Q₇ andQ₈ are each independently selected from a C₁-C₆₀ alkyl group and aC₆-C₆₀ aryl group; b1 to b4 are each independently selected from 1, 2,3, and 4; L₁ is selected from a monodentate ligand and a bidentateligand; a1 is selected from 0, 1, and 2; and * indicates a binding siteto a neighboring atom.
 2. The organometallic compound of claim 1,wherein M is selected from iridium (Ir), platinum (Pt), osmium (Os),ruthenium (Ru), rhodium (Rh), palladium (Pd), copper (Cu), silver (Ag),gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu),terbium (Tb), and thulium (Tm).
 3. The organometallic compound of claim1, wherein M is selected from Ir, Pt, and Os.
 4. The organometalliccompound of claim 1, wherein A₁ to A₄ are each independently selectedfrom a benzene group, a naphthalene group, a pyrrole group, an imidazolegroup, a pyrazole group, a thiazole group, an isothiazole group, anoxazole group, an isoxazole group, a triazole group, an indazole group,a tetrahydroindazole group, a pyridine group, a thiazine group, anoxazine group, a pyrimidine group, a pyrazine group, a pyridazine group,a triazine group, a quinoline group, an isoquinoline group, aquinoxaline group, a quinazoline group, naphthyridine group, an indolegroup, a benzimidazole group, a benzothiazole group, a benzoisothiazolegroup, a benzoxazole group, a benzoiso-oxazole group, a benzothiazinegroup, a benzoxazine group, a dibenzofuran group, and a dibenzothiophenegroup; at least one selected from A₃ and A₄ is selected from a pyrrolegroup, an imidazole group, a pyrazole group, a thiazole group, anisothiazole group, an oxazole group, an isoxazole group, a triazolegroup, an indazole group, a tetrahydroindazole group, a pyridine group,a thiazine group, an oxazine group, a pyrimidine group, a pyrazinegroup, a pyridazine group, a triazine group, a quinoline group, anisoquinoline group, a quinoxaline group, a quinazoline group,naphthyridine group, an indole group, a benzimidazole group, abenzothiazole group, a benzoisothiazole group, a benzoxazole group, abenzoiso-oxazole group, a benzothiazine group, and a benzoxazine group.5. The organometallic compound of claim 1, wherein A₁ to A₄ are eachindependently selected from a benzene group, a naphthalene group, apyridine group, a pyrimidine group, a pyrazine group, a quinoline group,an isoquinoline group, a dibenzofuran group, and a dibenzothiophenegroup; and at least one selected from A₃ and A₄ is selected from apyridine group, a pyrimidine group, a pyrazine group, a quinoline group,and an isoquinoline group.
 6. The organometallic compound of claim 1,wherein Y₁ to Y₃ are each independently selected from a single bond anda divalent linking group, at least one selected from Y₁ to Y₃ is adivalent linking group; and the divalent linking group is represented byone selected from *—O—*′, *—S—*′, and one of Formulae 8-1 to 8-18:

wherein, in Formulae 8-1 to 8-18, R₈₁ to R₈₈ are each independentlyselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxygroup; a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a phenyl group, a naphthyl group, a pyridinylgroup, and a pyrimidinyl group; a phenyl group, a naphthyl group, afluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a pyrrolyl group, a thiophenyl group, a furanyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolylgroup, an indolyl group, an indazolyl group, a purinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, and an imidazopyridinyl group; and aphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, and animidazopyridinyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂,—Si(CH₃)₃, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, afluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a pyrrolyl group, a thiophenyl group, a furanyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolylgroup, an indolyl group, an indazolyl group, a purinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, and an imidazopyridinyl group; n81 isselected from 1, 2, 3, 4, and 5; and * and *′ each independentlyindicate a binding site to a neighboring atom.
 7. The organometalliccompound of claim 1, wherein Y₁ to Y₃ are each independently selectedfrom a single bond and a divalent linking group, at least one selectedfrom Y₁ to Y₃ is a divalent linking group; and the divalent linkinggroup is represented by one selected from *—O—*′, *—S—*′ and one ofFormulae 9-1 to 9-70:

wherein, in Formulae 9-1 to 9-70, Ph refers to a phenyl group; 2-pyrrefers to a 2-pyridinyl group, 3-pyr refers to a 3-pyridinyl group, and4-pyr refers to a 4-pyridinyl group; and * and *′ each independentlyindicate a binding site to a neighboring atom.
 8. The organometalliccompound of claim 1, wherein Y₂₁ and Y₂₂ are each independently selectedfrom a methylene group, an ethylene group, and a propylene group; and amethylene group, an ethylene group, and a propylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,—CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, and a C₁-C₂₀ alkyl group; anda21 and a22 are each independently selected from 0, 1, 2, and
 3. 9. Theorganometallic compound of claim 1, wherein R₂₁=R₂₂=R₂₃; R₂₁=R₂₂, andR₂₂≠R₂₃; or R₂₁≠R₂₂, R₂₂≠R₂₃, and R₂₃≠R₂₁.
 10. The organometalliccompound of claim 1, wherein R₂₁ to R₂₇ are each independently selectedfrom: hydrogen, deuterium, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxygroup; a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclooctyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthylgroup, a pyridinyl group, and a pyrimidinyl group; a cyclopentyl group,a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, anadamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, and an imidazopyrimidinyl group; and a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclooctyl group, anadamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, and an imidazopyrimidinyl group, each substituted with at leastone selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃,—CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclooctyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthylgroup, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a pyrrolyl group, a thiophenyl group, a furanyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolylgroup, an indolyl group, an indazolyl group, a purinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, an imidazopyridinyl group, and animidazopyrimidinyl group.
 11. The organometallic compound of claim 1,wherein R₂₁ to R₂₇ are each independently selected from: hydrogen,deuterium, a methyl group, an ethyl group, an n-propyl group, aniso-propyl group, an n-butyl group, an iso-butyl group, a sec-butylgroup, a tert-butyl group, an n-pentyl group, an iso-pentyl group, asec-pentyl group, and a tert-pentyl group; a methyl group, an ethylgroup, an n-propyl group, an iso-propyl group, an n-butyl group, aniso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentylgroup, an iso-pentyl group, a sec-pentyl group, and a tert-pentyl group,each substituted with at least one selected from deuterium and a phenylgroup; a phenyl group and a naphthyl group; and a phenyl group and anaphthyl group, each substituted with at least one selected fromdeuterium, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a C₁-C₂₀ alkyl group,and a phenyl group.
 12. The organometallic compound of claim 1, whereinZ₁ and Z₂ are each independently represented by one of Formulae 2-11 to2-20:

wherein, in Formulae 2-11 to 2-20, R₂₁ to R₂₃ are each independentlyselected from a methyl group, an ethyl group, an n-propyl group, aniso-propyl group, an n-butyl group, an iso-butyl group, a sec-butylgroup, a tert-butyl group, a phenyl group, and a naphthyl group; and *indicates a binding site to a neighboring atom.
 13. The organometalliccompound of claim 1, wherein Z₁ and Z₂ are each independentlyrepresented by one of Formulae 2-21 to 2-34:

wherein, in Formulae 2-21 to 2-34, Et refers to an ethyl group; Phrefers to a phenyl group; and * indicates a binding site to aneighboring atom.
 14. The organometallic compound of claim 1, wherein d1and d2 are each independently selected from 0, 1, and 2; and at leastone selected from d1 and d2 is selected from 1 and
 2. 15. Theorganometallic compound of claim 1, wherein R₁ to R₄ are eachindependently selected from hydrogen, deuterium, a C₁-C₂₀ alkyl group,and a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxygroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a cyclopentyl group,a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, anadamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinylgroup; a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, an imidazopyridinyl group, and an imidazopyrimidinyl group; and acyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctylgroup, an adamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, and an imidazopyrimidinyl group, each substituted with at leastone selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃,—CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclooctyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthylgroup, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a pyrrolyl group, a thiophenyl group, a furanyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolylgroup, an indolyl group, an indazolyl group, a purinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, an imidazopyridinyl group, and animidazopyrimidinyl group.
 16. The organometallic compound of claim 1,wherein R₁ to R₄ are each independently selected from hydrogen,deuterium, a methyl group, an ethyl group, an n-propyl group, aniso-propyl group, an n-butyl group, an iso-butyl group, a sec-butylgroup, a tert-butyl group, an n-pentyl group, an iso-pentyl group, asec-pentyl group, and a tert-pentyl group; a phenyl group and acarbazolyl group; and a phenyl group, a naphthyl group, and a carbazolylgroup, each substituted with at least one selected from a C₁-C₂₀ alkylgroup and a phenyl group.
 17. The organometallic compound of claim 1,wherein the organometallic compound represented by Formula 1 isrepresented by one of Formulae 1-1 to 1-3:

wherein, in Formulae 1-1 to 1-3, M, A₁ to A₄, X₁ to X₄, Z₁, Z₂, d1, d2,R₁ to R₄, b1 to b4, L₁, and a1 are the same as defined in connectionwith Formula 1; and Y₁ to Y₃ are each independently a divalent linkinggroup.
 18. The organometallic compound of claim 1, wherein theorganometallic compound represented by Formula 1 is selected fromCompounds 1 to 18 and 20 to 37:

wherein, in Compounds 1 to 18 and 20 to 37, TMS refers to atrimethylsilyl group.
 19. An organic light-emitting device comprising afirst electrode; a second electrode; and an organic layer disposedbetween the first electrode and the second electrode, wherein theorganic layer comprises an emission layer and at least oneorganometallic compound of claim
 1. 20. The organic light-emittingdevice of claim 19, wherein the emission layer comprises theorganometallic compound.